Methanol → (S)-2,3-bis(tert-butyldimethylsilyloxy)propan-1-ol

HRID 1009098ノート

反応式

HRID 1009098 の反応式
COC1C=CC(C([O:9][CH2:10][C@H:11]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=O)=CC=1.CC(C[AlH]CC(C)C)C.CO.[K].[Na]>C(Cl)Cl>[Si:22]([O:21][C@H:11]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH2:10][OH:9])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 16211683Potassium alloy, nonbase, K,NaHCID 44240216(S)-2,3-bis(tert-butyldimethylsilyloxy)propyl 4-methoxybenzoate

生成物 1

HCID 46201106(S)-2,3-bis(tert-butyldimethylsilyloxy)propan-1-ol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a 1.0 L RB flask containing (S)-2,3-bis(tert-butyldimethylsilyloxy)propyl 4-methoxybenzoate (9.200 g, 20 mmol) was added DCM (100 mL) and the mixture was allowed to stir at −78° C. for 5 minutes. At this time, DIBAL-H (1.0 M, hexanes) (61 ml, 61 mmol) was added via a syringe. The reaction was allowed to stir for 30 min and then quenched with MeOH (4.1 ml, 101 mmol). Sodium potassium tartate (sat, 200 mL) and DCM (100 mL) was added and the solution was allowed to warm to 23° C. and stirred for 3 h. The aq. layer was extracted with DCM (3 100 mL). The combined organics were washed with brine and dried with sodium sulfate and concentrated to give a residue.

後処理

  1. stirringto stir for 30 min
  2. temperatureto warm to 23° C.
  3. stirringstirred for 3 h
  4. extractionThe aq. layer was extracted with DCM (3 100 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customto give a residue

出典と根拠

ORDレコード
ord-ee0171770acb409f844c32297c1eb0f5
出典データセット
uspto-grants-2011_07
特許番号
US07973047B2

反応ノート

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