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

HRID 1009098

반응식

HRID 1009098 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ee0171770acb409f844c32297c1eb0f5
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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