Tert-Butylamine → HCID 71089303、化合物

HRID 1410324ノート

反応式

HRID 1410324 の反応式
[CH3:1][C:2]1[CH2:3][C:4]2[C:5]([CH:45]=1)=[CH:6][C:7]1[C:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:9]3[C:14]([C:15]=1[CH:16]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3.C([Li])CCC.C(N)(C)(C)C.[C:56]([NH:60][Si:61](C1C2C(=CC3C(CCCCCCCCCCCCCC)(CCCCCCCCCCCCCC)C4C(C=3C=2)=CC=CC=4)C=C1C)([CH3:63])[CH3:62])([CH3:59])([CH3:58])[CH3:57]>C(OCC)C>[C:56]([NH:60][Si:61]([CH:45]1[C:5]2=[CH:6][C:7]3[C:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:9]4[C:14]([C:15]=3[CH:16]=[C:4]2[CH:3]=[C:2]1[CH3:1])=[CH:13][CH:12]=[CH:11][CH:10]=4)([CH3:63])[CH3:62])([CH3:59])([CH3:58])[CH3:57]

参加物

6

反応物 4

HCID 6385Tert-ButylamineHCID 71089355HCID 71089355、化合物HCID 866947952-Methyl-9,9-ditetradecyl-3,9-dihydrocyclopenta[b]fluoreneHCID 178418339Butyllithium

生成物 1

HCID 71089303HCID 71089303、化合物収率 92.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

In a 250 mL round flask, 2-methyl-9,9-ditetradecyl-3,9-dihydrocyclopenta[b]fluorene (4.9 g, 8.0 mmol) was dissolved in 100 mL of anhydrous diethyl ether, and then the temperature was lowered to −78° C. Then, n-butyllithium (1.6M hexane solution, 5.5 mL) was slowly injected thereto, followed by stirring at room temperature for 12 hours. After volatile materials were removed by vacuum, 100 mL of n-hexane was added to the mixture to lower the reactor temperature to −78° C., followed by addition of dichlorodimethylsilane (2.9 g). The temperature was again raised to room temperature, followed by stirring for 24 hours, and then salts were removed through filtering. Then, volatile materials were removed by vacuum. The product was again inputted to a 250 mL round flask, and dissolved in 100 mL of diethyl ether. The temperature was lowered to −78° C., and tert-butylamine (1.8 g, 24.1 mmol) was added thereto. The temperature was raised to room temperature, followed by stirring for 12 hours, and then volatile materials were completely removed by vacuum. Then, 200 mL of n-hexane was added to dissolve the resultant material, and salts were removed through filtering. The solvent was removed, to thereby obtain 5.5 g of a mixture of N-tert-butyl-1-(9,9-ditetradecyl-2-methyl-3,9-dihydrocyclopenta[b]fluoren-3-yl)-1,1-dimethylsilanamine and N-tert-butyl-1-(9,9-ditetradecyl-2-methyl-1,9-dihydrocyclopenta[b]fluoren-1-yl)-1,1-dimethylsilanamine (ratio=˜1:1), (yield: 92.7%), as high viscous material.

後処理

  1. customwas lowered to −78° C
  2. customAfter volatile materials were removed by vacuum, 100 mL of n-hexane
  3. additionwas added to the mixture
  4. customto −78° C.
  5. additionfollowed by addition of dichlorodimethylsilane (2.9 g)
  6. temperatureThe temperature was again raised to room temperature
  7. stirringby stirring for 24 hours
  8. customsalts were removed
  9. filtrationthrough filtering
  10. customThen, volatile materials were removed by vacuum
  11. customThe product was again inputted to a 250 mL round flask
  12. dissolutiondissolved in 100 mL of diethyl ether
  13. customwas lowered to −78° C.
  14. temperatureThe temperature was raised to room temperature
  15. stirringby stirring for 12 hours
  16. customvolatile materials were completely removed by vacuum
  17. additionThen, 200 mL of n-hexane was added
  18. dissolutionto dissolve the resultant material, and salts
  19. customwere removed
  20. filtrationthrough filtering
  21. customThe solvent was removed

出典と根拠

ORDレコード
ord-8b9aa4cc5e544deb9806a7c96db8f1bd
出典データセット
uspto-grants-2014_12
特許番号
US08921499B2

反応ノート

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