1,4-Butanediol → 4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol

HRID 1776137Notes

Reaction equation

HRID 1776137 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:14]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:18]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 80641,4-ButanediolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of butane-1,4-diol (180.0 g, 2.0 mol), triethylamine (242.4 g, 2.4 mol) in DCM (1500 mL) was dropwised tert-butylchlorodimethylsilane (306 g, 2.03 mol) in 500 mL DCM, the mixture was stirred for about 1 hr at 0° C., then was warmed at RT for overnight. the reaction was washed with water (500 mL×3) and brine (500×3 mL), dried over Na2SO4 and concentrated to give the desired compound of 4-(tert-butyl dimethylsilyl oxy) butan-1-ol

Workup

  1. temperaturewas warmed at RT for overnight
  2. washthe reaction was washed with water (500 mL×3) and brine (500×3 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07109c11fbca474fb9244ff7a034e8d6
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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