Diethyl Ether → 2-(4-(Tert-butyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 407601

反応式

HRID 407601 の反応式
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([C:9]([NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCOCC>S(Cl)(Cl)=O>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([C:9]2[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 3283Diethyl EtherHCID 3200764-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide

生成物 1

HCID 3200722-(4-(Tert-butyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole収率 57.1%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

A mixture of 101b (1000 g, crude) in thionyl chloride (1.5 L) was refluxed for 1 hour. The reaction mixture was cooled to room temperature and poured into 500 mL of stirred Et2O, during which time a white precipitate formed. The precipitate was collected by filtration and washed with Et2O, dissolved in 500 mL of water and neutralized with 25 percent NaOH. The yellow aqueous solution was extracted with EtOAC (3×500 mL) and the combined organic phase was washed with 500 mL of brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 101c (530 g, 40.8% over 3 steps) as a white solid. 1HNMR (300 MHz, CDCl3) δ 7.87 (d, J=8.4 Hz, 2H), 7.41 (d, J=8.4 Hz, 2H), 4.08 (s, 2H), 1.37 (s, 6H), 1.33 (s, 9H).

後処理

  1. temperaturewas refluxed for 1 hour
  2. customformed
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with Et2O
  5. dissolutiondissolved in 500 mL of water and neutralized with 25 percent NaOH
  6. extractionThe yellow aqueous solution was extracted with EtOAC (3×500 mL)
  7. washthe combined organic phase was washed with 500 mL of brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8707473eb7364e0aaae056537de84b53
出典データセット
uspto-grants-2014_06
特許番号
US08754077B2

関連ノート

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