Triethylamine → (R)-4-((tert-butyldiphenylsilyl)oxy)butan-2-ol

HRID 1003600Notes

Reaction equation

HRID 1003600 reaction equation
[CH2:1]([OH:6])[CH2:2][C@H:3]([OH:5])[CH3:4].C(N(CC)CC)C.[C:14]([Si:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)Cl)([CH3:17])([CH3:16])[CH3:15].[NH4+].[Cl-]>C(Cl)Cl>[O:6]([CH2:1][CH2:2][C@H:3]([OH:5])[CH3:4])[Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 637497(-)-1,3-Butanediol

Product 1

HCID 12032996(R)-4-((tert-butyldiphenylsilyl)oxy)butan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-1,3-butanediol (2 g), triethylamine (4 mL) and t-butyldiphenylchlorosilane (6.7 g) in CH2Cl2 (80 mL) was stirred at r.t. for 15 h. Saturated NH4Cl was added and the mixture was extracted with ethyl acetate. The combined organics were dried (MgSO4) and concentrated. Flash chromatography of the residue (9:1 hexane/ethyl acetate) provided the title compound as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organics were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-354fc6f1ee274c7591d597129c474358
Source dataset
uspto-grants-2000_04
Patent number
US06046217

Reaction notes

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