Chlorotrimethylsilane → 2,3-Bis(hydroxymethyl)cyclobutanol

HRID 5957Notes

Reaction equation

HRID 5957 reaction equation
CC([Si](C)(C)[O:6][CH2:7][CH:8]1[CH:11]([CH2:12][O:13][Si](C(C)(C)C)(C)C)[CH2:10][CH:9]1[OH:21])(C)C.Cl[Si](C)(C)C>CO>[OH:6][CH2:7][CH:8]1[CH:11]([CH2:12][OH:13])[CH2:10][CH:9]1[OH:21]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 197942582,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanol

Product 1

HCID 540835352,3-Bis(hydroxymethyl)cyclobutanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanol (6.3 g, 17.5 mmol) from Step C was combined with 5.3 mL (43 mmol) of chlorotrimethyl-silane in 103 mL of methanol. The reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 0.5 h then concentrated under reduced pressure to an oil. Residual chlorotrimethylsilane was removed by co-evaporation with methanol (3×30 mL) to give title compound in quantitative yield and this crude product was carried on to the next step without purification; 1H NMR (CD3OD) δ 1.94-2.14 (m, 2H), 2.17-2.37 (m, 2H), 3.53 (d, 2H), 3.68 (dd, 1H), 3.85 (dd, 1H), 4.39 (m, 1H); MS DCI-NH3M/Z: 133 (M+H)+, 150 (M+NH4)+.

Workup

  1. concentrationthen concentrated under reduced pressure to an oil
  2. customResidual chlorotrimethylsilane was removed by co-evaporation with methanol (3×30 mL)

Sources & evidence

ORD record
ord-a3501c466ca1436bb389403a5114d62c
Source dataset
uspto-grants-1993_09
Patent number
US05246931

Reaction notes

Loading…