Diazomethane → Ethyl 2-(4-tert-butylphenyl)cyclopropanecarboxylate

HRID 446760

Reaction equation

HRID 446760 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:20])=[N-]>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:20][CH:12]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 136011774-tert-Butylcinnamic acid ethyl ester

Product 1

HCID 615698Ethyl 2-(4-tert-butylphenyl)cyclopropanecarboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

To a −40° C. solution of (E)-ethyl 3-(4-tert-butylphenyl)acrylate (1.0 g, 4.3 mol) in ether (20 mL), freshly prepared diazomethane was added dropwise over 10 minutes. Pd(OAc)2 (30 mg, 0.133 mol) was then added. The reaction mixture was stirred for another 10 min at −40° C., and then filtered through a pad of Celite® and precipitate washed with ether. The filtrate was concentrated in vacuo and the crude material was then purified via silica gel column chromatography to afford ethyl 2-(4-tert-butylphenyl)cyclopropanecarboxylate (0.9 g, 84%) as an oil.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. customprecipitate
  3. washwashed with ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude material was then purified via silica gel column chromatography

Sources & evidence

ORD record
ord-7ba020a4d3a34f9290a331804c6f7c81
Source dataset
uspto-grants-2013_07
Patent number
US08481532B2

Linked notes

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