Pentamethylsilylamine → 1-(3-(2-(Dimethylamino)ethenyl)-2,2-dimethylcyclopropyl)-2-propanone

HRID 1758576Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[CH:4]([CH2:5][C:6](=[O:8])[CH3:7])[CH:3]1[CH2:9][CH:10]=O.C[Si]([N:17]([CH3:19])[CH3:18])(C)C>>[CH3:18][N:17]([CH3:19])[CH:10]=[CH:9][CH:3]1[CH:4]([CH2:5][C:6](=[O:8])[CH3:7])[C:2]1([CH3:12])[CH3:1]

Participants

Reactant 2

HCID 74965Pentamethylsilylamine

HCID 10888310Cyclopropaneacetaldehyde, 2,2-dimethyl-3-(2-oxopropyl)-

Product 1

HCID 545240321-(3-(2-(Dimethylamino)ethenyl)-2,2-dimethylcyclopropyl)-2-propanoneYield 86.1%

Procedure

To 6.7 g of 2,2-dimethyl-3-(2-oxopropyl)cyclopropylacetaldehyde at 0° C. was added 5.2 g of trimethylsilyldimethylamine over a 5 min period. The resulting product was distilled through a spiral bantamware column to yield 6.7 g of the desired product having a boiling point of 85°-90° at 1 mm Hg.

Workup

distillationThe resulting product was distilled through a spiral bantamware column

Sources & evidence

ORD record: ord-554d56a6600247dcaf0aa9f9ec8beaed
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374275

Reaction notes

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