Reaction #6053

Reaction equation

2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanol

2.3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanol

chlorotrimethyl-silane

→

title compound

2,3-Bis(hydroxymethyl)cyclobutanol

Solvents

methanol

Conditions

Workup

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

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)+.

Source