Diisopropyldichlorosilane → HCID 66747067, compound

HRID 1926550Notes

Reaction equation

HRID 1926550 reaction equation
OC[Si](C(C)C)(C(C)C)C(C)C.[CH:13]1([Si:16]([C:23]([OH:26])(C)[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH2:15][CH2:14]1.Cl[Si](Cl)(C(C)C)C(C)C.C(OC=C[Li])C.C1([Li])CC1.C1([Si](C(OCC)=C)(C(C)C)C(C)C)CC1>CC(C)=O>[C:23]([Si:16]([CH:13]1[CH2:15][CH2:14]1)([CH:20]([CH3:21])[CH3:22])[CH:17]([CH3:18])[CH3:19])(=[O:26])[CH3:24]

Participants

8

Reactant 6

HCID 2758384DiisopropyldichlorosilaneHCID 15681847HCID 15681847, compoundHCID 46900825HCID 46900825, compoundHCID 66747401HCID 66747401, compoundHCID 178506812HCID 178506812, compoundHCID 178506908HCID 178506908, compound

Product 1

HCID 66747067HCID 66747067, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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

Sources & evidence

ORD record
ord-079b55941a71456a9647922d309eb21d
Source dataset
uspto-grants-2012_05
Patent number
US08182781B2

Reaction notes

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