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

HRID 1009098

Reaction equation

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]

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-ee0171770acb409f844c32297c1eb0f5
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973047B2

Linked notes

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