4-Bromoanisole → HCID 11381397、化合物

HRID 2424175ノート

反応式

HRID 2424175 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+]>O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9](=[O:15])[CH:8]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH2:7][CH2:6]2

参加物

6

反応物 3

HCID 77304-BromoanisoleHCID 114470756,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-oneHCID 23676156Sodium t-butoxide

生成物 1

HCID 11381397HCID 11381397、化合物収率 78.8%

試薬・触媒・溶媒 2

HCID 634876Binap, (A+-)-触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

The title compound was synthesized by referring to J. Am. Chem. Soc., 1997, 119 (45), 11108. To a solution of 6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one (11.9 g) in tetrahydrofuran (200 ml) were sequentially added 4-bromoanisole (16.2 g), sodium tert-butoxide (11.1 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.3 g) and tris(dibenzylidene)acetone dipalladium(0) (792 mg), and the solution was stirred for 1.5 hours at 75° C. under a nitrogen atmosphere. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo; the resulting crude crystal was suspended in diethyl ether and then filtered. The mother liquor was concentrated in vacuo, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate system); the resulting crystal was suspended in diethyl ether, then filtered, and combined to provide the title compound (14.2 g).

後処理

  1. customThe title compound was synthesized
  2. extractionThe solution was extracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. filtrationfiltered
  7. concentrationThe mother liquor was concentrated in vacuo
  8. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate system)
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-ea921849fcf7446597b7016f38d7410a
出典データセット
uspto-grants-2011_06
特許番号
US07960412B2

反応ノート

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