Triethylamine → 3-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropan-1-ol

HRID 1398534Notes

Reaction equation

HRID 1398534 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].C(N(CC)CC)C.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl>[C:15]([Si:19]([CH3:21])([CH3:20])[O:4][CH2:3][C:2]([CH3:7])([CH3:1])[CH2:5][OH:6])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 31344Neopentyl glycol

Product 1

HCID 590121383-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropan-1-olYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2-dimethyl-propane-1,3-diol (5.0 g, 48 mmol) in DCM (20 mL) was added triethylamine (14.6 g, 144.3 mmol) and tert-butyl-chloro-dimethyl-silane (7.2 g, 48.1 mmol). The solution was stirred overnight at room temperature. The reaction mixture was then washed with water (×3) and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound (6.1 g, 58%): 1H NMR (CDCl3, 400 MHz) delta 0.04 (s, 6H), 0.86 (s, 6H), 0.87 (s, 9H), 2.94 (s, 1H), 3.43 (s, 4H).

Workup

  1. washThe reaction mixture was then washed with water (×3)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-543bc7188b0747d688f43dc8e3aff09c
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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