Water → (2R)-3-[(tert-butyldimethylsilyl)oxy]-2-methylpropan-1-ol

HRID 329785Notes

Reaction equation

HRID 329785 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([CH3:15])[C:11](OC)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.O>ClCCl>[Si:1]([O:8][CH2:9][C@H:10]([CH3:15])[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 11128183methyl (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropionateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10998135(2R)-3-[(tert-butyldimethylsilyl)oxy]-2-methylpropan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropionate (10.0 g; 43.1 mmol) was dissolved in anhydrous dichloromethane (100 ml), and a hexane solution (100 ml) of 1M diisobutylaluminum hydride was dropwise added thereto at a temperature below 0° C. in an argon stream. After stirring for 30 minutes, water (20 ml) was added thereto, and the resultant mixture was stirred for 1 hour, followed by separation of the organic layer. The aqueous layer was extracted with dichloromethane, and the extracts were combined together with the organic layer. The solvent was distilled under reduced pressure to give (R)-(+)-3-(t-butyldimethylsilyloxy)-2-methyl-1-propanol (7.9 g; yield, 90%) as a colorless oil. A portion of the oil was distilled to give a purified product (bath temperature: 112° C./17 mmHg).

Workup

  1. customat a temperature below 0° C.
  2. customfollowed by separation of the organic layer
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-5465ccc2c555483ebe1a5623e29db14c
Source dataset
uspto-grants-1990_01
Patent number
US04892961

Reaction notes

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