Imidazole → 4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol

HRID 1842217Notes

Reaction equation

HRID 1842217 reaction equation
N1C=CN=C1.[CH2:6]([OH:11])[CH2:7][CH2:8][CH2:9][OH:10].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(OCC)C>CN(C=O)C.ClCCl.O>[Si:12]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][OH:11])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 80641,4-ButanediolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 1864034-(Dimethyl-tert-butylsilyl)oxybutan-1-ol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Imidazole (6.77 g) was added to a solution containing 1,4-butanediol (58.8 mL) in DMF (60.0 mL) at room temperature. A solution of tert-butyldimethylsilyl chloride (10.0 g) in dichloromethane (5.0 mL) was added dropwise, and the mixture was stirred at the same temperature for three hours. Diethyl ether and water were added to the reaction solution. The organic layer was separated, washed with water and a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated to obtain the title compound (13.4 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated sodium chloride solution and then dried over anhydrous magnesium sulfate
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fcb79ee1425d4b3fa4e2506993279478
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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