Lithium diisopropylamide → 3-[5-(Benzo[b]thien-2-yl)2,4-dimethoxyphenyl]-1-(4-tert-butyldimethylsiloxy-3,5-dimethoxyphenyl)-2-propen-1-one

HRID 1792974

反応式

HRID 1792974 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:19](=[O:21])[CH3:20])[CH:6]=[C:7]([O:17][CH3:18])[C:8]=1[O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C([N-]C(C)C)(C)C.[Li+].[S:30]1[C:34]([C:35]2[C:36]([O:45][CH3:46])=[CH:37][C:38]([O:43][CH3:44])=[C:39]([CH:42]=2)[CH:40]=O)=[CH:33][C:32]2[CH:47]=[CH:48][CH:49]=[CH:50][C:31]1=2>O1CCCC1>[S:30]1[C:34]([C:35]2[C:36]([O:45][CH3:46])=[CH:37][C:38]([O:43][CH3:44])=[C:39]([CH:40]=[CH:20][C:19]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:11])[CH3:12])=[C:7]([O:17][CH3:18])[CH:6]=3)=[O:21])[CH:42]=2)=[CH:33][C:32]2[CH:47]=[CH:48][CH:49]=[CH:50][C:31]1=2

参加物

5

反応物 3

HCID 2724682Lithium diisopropylamideHCID 161159165-Benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehydeHCID 220255931-(4-((tert-Butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)ethanone

生成物 1

HCID 696209063-[5-(Benzo[b]thien-2-yl)2,4-dimethoxyphenyl]-1-(4-tert-butyldimethylsiloxy-3,5-dimethoxyphenyl)-2-propen-1-one収率 20%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Ex-59B: To a solution of 3′,5′-dimethoxy-4′-(tert-butyldimethylsiloxy)acetophenone, from Ex-59A (0.5 g, 1.6 mmol) in tetrahydrofuran (10 mL) chilled with ice/water was added lithium diisopropylamide (2 M, 0.8 mL, 1.6 mmol). The mixture was stirred for 20 minutes while chilled. Then 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde, from Ex-6A,(0.48 g, 1.6 mmol) in tetrahydrofuran (6 mL) was added, and the mixture was stirred at room temperature for 2 hours. Upon quenching with water, the mixture was extracted with dichloromethane. The organic phase was dried and evaporated. Crystallization from ethanol gave 0.19 g (20%) of the desired 3-[5-(benzo[b]thien-2-yl)2,4-dimethoxyphenyl]-1-(4-tert-butyldimethylsiloxy-3,5-dimethoxyphenyl)-2-propen-1-one as a yellow solid.

後処理

  1. temperaturewhile chilled
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customUpon quenching with water
  4. extractionthe mixture was extracted with dichloromethane
  5. customThe organic phase was dried
  6. customevaporated
  7. customCrystallization from ethanol

出典と根拠

ORDレコード
ord-7211d0c745c549738a94877ba304ff6d
出典データセット
uspto-grants-2006_07
特許番号
US07078431B2

関連ノート

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