tert-Butyldimethylsilyl chloride → HCID 11367157, compound

HRID 1926553Notes

Reaction equation

HRID 1926553 reaction equation
[C:1]([Si:5]([C:8]([OH:11])(C)[CH3:9])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C([Si](Cl)(C)C)(C)(C)C.C(OC=C[Li])C>CC(C)=O>[C:8]([Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])(=[O:11])[CH3:9]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 46900816HCID 46900816, compoundHCID 178506908HCID 178506908, compound

Product 1

HCID 11367157HCID 11367157, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for the preparation of acetylsilanes (see Example 1) tert-butyl(1-hydroxy-1-methylethyl)dimethylsilane was prepared from tert-butylchlorodimethylsilane (5.00 g, 33.2 mmol) and ethoxyvinyl lithium (prepared from ethyl vinyl ether (3.11 g, 43.1 mmol) and tert-butyl lithium (1.9 M in pentane, 22.7 ml, 43.1 mmol) in THF (50 ml)). The crude material was hydrolysed with acetone/1 N HCl (2:1, 60 ml), and purified by silica-gel chromatography (silica-gel 40-63 μm, hexane/EtOAc, 9:1) to afford 2.13 g (41% over 2 steps) of acetyl(tert-butyl)dimethylsilane, of which 1.44 g, (9.10 mmol) was reacted according to Example 1 with methyl lithium (1.6 M in Et2O, 28.4 ml, 45.4 mmol) to provide after purification by silica-gel flash chromatography (silica-gel 15-40 μm, hexane/EtOAc, 9:1) 590 mg (37%) of the odoriferous title compound.

Workup

  1. custompurified by silica-gel chromatography (silica-gel 40-63 μm, hexane/EtOAc, 9:1)

Sources & evidence

ORD record
ord-50b243d8c94547a3a7674b8337205258
Source dataset
uspto-grants-2012_05
Patent number
US08182781B2

Reaction notes

Loading…