Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-Ethyl 3-(1-((tert-butoxycarbonyl)amino)cyclopropyl)acrylate

HRID 635058

Reaction equation

HRID 635058 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH:12]=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH2:17][CH3:18])=[O:15]>ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1(/[CH:12]=[CH:19]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 10352385(1-Formylcyclopropyl)carbamic acid tert-butyl ester

Product 1

HCID 11777121(E)-Ethyl 3-(1-((tert-butoxycarbonyl)amino)cyclopropyl)acrylateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Tert-butoxycarbonylaminocyclopropane carbaldehyde (10.99 g, 59.3 mmol) and (carbethoxymethylene) triphenylphosphorane (27.6 g, 75.2 mmol) were dissolved in dichloromethane (300 ml) and heated under reflux for 4 hours. After evaporating the solvent, the resulting residue was applied to a silica gel chromatography column and eluted with an eluant of n-hexane:ethyl acetate=9:1, to thereby obtain 9.23 g (61%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customAfter evaporating the solvent
  4. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-5dd4c89717ee406cb2fa55f2bc65756a
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Linked notes

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