Cyclopropanecarbonyl chloride → 73252-24-1

HRID 1729495Notes

Reaction equation

HRID 1729495 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].CC(C)([O-])C.[K+].[CH:15]1([C:18](Cl)=[O:19])[CH2:17][CH2:16]1>C1COCC1>[CH:15]1([C:18]2[O:19][CH:2]=[N:1][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 533707Ethyl isocyanoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 1349699673252-24-1

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of ethyl isocyanoacetate (13.4 g) in THF (65 ml) was added dropwise to a stirred solution of potassium tert-butoxide (14.5 g) in THF (97 ml) at 0° C. Cyclopropanecarboxylic acid chloride (5.4 ml) was added dropwise at below 10° C. and the solvent evaporated. Water (68 ml) and acetic acid (3.4 ml) was added to the mixture, then diisopropyl ether (2×150 ml) was added and the layers separated. The aqueous layer was further extracted with diisopropyl ether (2×150 ml) and the combined organic extracts were dried. Evaporation of the solvent afforded the title compound as a yellow oil (8.3 g).

Workup

  1. customthe solvent evaporated
  2. additionWater (68 ml) and acetic acid (3.4 ml) was added to the mixture
  3. additiondiisopropyl ether (2×150 ml) was added
  4. customthe layers separated
  5. extractionThe aqueous layer was further extracted with diisopropyl ether (2×150 ml)
  6. customthe combined organic extracts were dried
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4a41d2127e814b58a50a10c034260883
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

Loading…