HCID 66747067, compound → HCID 46900825, compound

HRID 1926551Notes

Reaction equation

HRID 1926551 reaction equation
[C:1]([Si:4]([CH:11]1[CH2:13][CH2:12]1)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])(=[O:3])[CH3:2].[CH3:14][Li]>>[CH:11]1([Si:4]([C:1]([OH:3])([CH3:14])[CH3:2])([CH:8]([CH3:9])[CH3:10])[CH:5]([CH3:6])[CH3:7])[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 66747067HCID 66747067, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 46900825HCID 46900825, compound

Procedure

According to the synthesis of 1-hydroxy-1-methylethyl(diisopropyl)methylsilane (Example 7), cyclopropyl(1-hydroxy-1-methylethyl)(diisopropyl)silane was prepared from dichloro(diisopropyl)silane (5.00 g, 27.0 mmol), ethoxyvinyl lithium (prepared from ethyl vinyl ether (2.17 g, 30.1 mmol) and tert-butyl lithium (1.9 M in pentane, 14.2 ml, 27.0 mmol) in THF (40 ml)) and cyclopropyl lithium (prepared according to Example 1 from bromocyclopropane (3.59 g, 29.7 mmol) and lithium (412 mg, 59.4 mmol) in Et2O). The crude cyclopropyl(1-ethoxyvinyl)(diisopropyl)silane was hydrolysed with acetone/1 N HCl (2:1, 72 ml), and purified by silica-gel flash chromatography (silica gel 40-63 μm, hexane/EtOAc, 9:1) to afford 2.11 g (39%) acetyl(cyclopropyl)(diisopropyl)silane. Reaction of acetyl(cyclopropyl)(diisopropyl)silane (1.00 g, 5.04 mmol) with methyl lithium (1.6 M in Et2O, 25.2 ml, 40.3 mmol) afforded after purification by silica-gel chromatography (silica gel 15-40 μm, hexane/EtOAc, 9:1) 590 mg (55%) of the odoriferous title compound.

Workup

  1. customafforded
  2. customafter purification by silica-gel chromatography (silica gel 15-40 μm, hexane/EtOAc, 9:1) 590 mg (55%) of the odoriferous title compound

Sources & evidence

ORD record
ord-c6b129b979064f46b4480899c0d492a5
Source dataset
uspto-grants-2012_05
Patent number
US08182781B2

Reaction notes

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