tert-Butyldimethylsilyl chloride → (2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol

HRID 1990149Notes

Reaction equation

HRID 1990149 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:9]([OH:13])[C@H:10]([OH:12])[CH3:11].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)C.O>[CH3:5][C:4]([Si:1]([CH3:3])([CH3:2])[O:13][CH2:9][C@H:10]([OH:12])[CH3:11])([CH3:7])[CH3:6]

Participants

7

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 259994R-(-)-1,2-Propanediol

Product 1

HCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-olYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(dimethyl)silyl chloride (5.90 g, 39.5 mmol) was added to a solution of (2R)-propane-1,2-diol (3.00 g, 39.5 mmol) in DCM (100 mL) followed by diisopropylethylamine (7.10 g, 55.3 mmol) and the reaction was stirred under argon for 72 h. The reaction was diluted with diethyl ether (500 mL) and water (140 mL) and the organic layer was separated then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:15 to 1:10 ethyl acetate:hexane, afforded the title compound as a colourless oil (6.00 g, 80%).

Workup

  1. customthe organic layer was separated
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by column chromatography
  6. washeluting with 1:15 to 1:10 ethyl acetate

Sources & evidence

ORD record
ord-22646d8516e743ebaa217a45b26b7e7c
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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