trans-2-Phenylcyclopropanecarboxylic acid → Ethanone, 1-[(1R,2R)-2-phenylcyclopropyl]-, rel- (9CI)

HRID 1183389Notes

Reaction equation

HRID 1183389 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][Li]>C(OCC)C>[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10](=[O:12])[CH3:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 237413trans-2-Phenylcyclopropanecarboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 6993787Ethanone, 1-[(1R,2R)-2-phenylcyclopropyl]-, rel- (9CI)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

trans-2-Phenyl-1-cyclopropanecarboxylic acid (2.0 g, 12.3 mmol) was dissolved in diethyl ether (40 mL) and cooled to 0° C. Methyllithium (1.6 M in hexanes, 16.8 mL, 27 mmol) was added dropwise and then the reaction stirred for 1 hour. The reaction was quenched with MeOH then submitted to standard aqueous workup and silica gel chromatography (0-40% EtOAc in hexanes) to afford the title compound.

Workup

  1. customThe reaction was quenched with MeOH

Sources & evidence

ORD record
ord-56fbbf3ed34849a89c9da97195fa9b2a
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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