tert-Butyldimethylsilyl chloride → HCID 86693774, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationThe reaction is concentrated in vacuo
- 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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