tert-Butyldimethylsilyl chloride → HCID 86693774, compound

HRID 245061Notes

Reaction equation

HRID 245061 reaction equation
[O:1]1[CH2:5][C@H:4]([OH:6])[C@@H:3]([OH:7])[CH2:2]1.[C:8]([Si:12]([CH3:15])([CH3:14])Cl)([CH3:11])([CH3:10])[CH3:9]>ClCCl>[Si:12]([O:6][C@H:4]1[CH2:5][O:1][CH2:2][C@@H:3]1[OH:7])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 641772HCID 641772, compound

Product 1

HCID 86693774HCID 86693774, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (3S,4S)-tetrahydrofuran-3,4-diol (9.35 g, 89.8 mmol), t-butyldimethylchlorosilane (14.9 g, 98.8 mmol), TEA (13.8 mL, 98.8 mmol), and dichloromethane (100 mL) is stirred at room temperature for 4 days. The reaction is concentrated in vacuo and purified on silica gel (330 g, 35-80% EtOAc/hexanes, observed on TLC using KMnO4 staining) to give 3.66 g (19%) of the title compound as a light yellow oil. GC-MS m/z 161 (M-tBu)+.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. custompurified on silica gel (330 g, 35-80% EtOAc/hexanes, observed on TLC using KMnO4 staining)

Sources & evidence

ORD record
ord-1d523e9390d54216bc3f9313aeafef46
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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