Methyl vinyl ketone → Spiro(4.5)dec-6-ene-8-one

HRID 1631850

Reaction equation

HRID 1631850 reaction equation
[CH:1]1([CH:6]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]([C:10]([CH3:12])=[O:11])=[CH2:9]>>[CH2:2]1[C:1]2([CH2:6][CH2:12][C:10](=[O:11])[CH:8]=[CH:9]2)[CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 70106Cyclopentanecarbaldehyde

Product 1

HCID 139772Spiro(4.5)dec-6-ene-8-oneYield 54%

Procedure

Piperidine enamine was prepared by a method analogous to that described in Organic Syntheses, Collective Volume 7, p 473, using 221.84 g of cyclopentane carbaldehyde instead of cyclooctane carbaldehyde. Through Michael addition of piperidine enamine to methyl vinyl ketone, cyclization by aldol condensation, dehydration, hydrolysis, and vacuum distillation for purification, there was obtained 173.4 g (yield 54%) of spiro[4.5]dec-6-en-8-one.

Workup

  1. customby aldol condensation, dehydration, hydrolysis, and vacuum distillation
  2. customfor purification

Sources & evidence

ORD record
ord-c5f62ab611364ee3909ce0b58766bf29
Source dataset
uspto-grants-2014_07
Patent number
US08791288B2

Linked notes

Loading…