Imidazole → (S)-4-(tert-butyldimethylsilyloxy)butan-2-ol

HRID 411253Notes

Reaction equation

HRID 411253 reaction equation
[CH2:1]([OH:6])[CH2:2][C@@H:3]([OH:5])[CH3:4].N1C=CN=C1.CN(C)C=O.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>ClCCl>[Si:17]([O:6][CH2:1][CH2:2][C@@H:3]([OH:5])[CH3:4])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 446973(+)-1,3-Butanediol

Product 1

HCID 10998136(S)-4-(tert-butyldimethylsilyloxy)butan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of (S)—(+)-1,3-butanediol (2.1 g, 23.3 mmol), imidazole (1.74 g, 25.6 mmol), and N,N-dimethylformamide (1.0 mL) in dichloromethane (40 mL) was treated with tert-butyl-dimethylsilyl chloride (3.68 g, 23.3 mmol). The reaction mixture was warmed to room temperature, stirred overnight, quenched with saturated aqueous ammonium chloride and extracted with dichloromethane. The combined dichloromethane layers were dried (MgSO4), filtered and concentrated to afford of the desired product of sufficient purity for subsequent use without further purification in near quantitative yield.

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined dichloromethane layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-52f880592c4b40639a7e41c83a8a1b86
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

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