Benzyl Bromide → 1,1-Dimethylethyl 1-(phenylmethyl)cyclopropanecarboxylate
Reaction equation
[Li+].CC([N-]C(C)C)C.[C:9]([O:13][C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH4+].[Cl-]>C1COCC1>[C:9]([O:13][C:14]([C:16]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]Participants
Procedure
To a stirring solution of LDA (11 mL, 22 mmol, 2 M in THF) in THF (40 mL) under nitrogen is added drop wise at −75° C. a THF solution (10 mL) of the title A compound, cyclopropanecarboxylic acid tert-butyl ester (2.85 g, 20 mmol). The resulting mixture is stirred for 5 h at −75° C. before the addition of a THF solution (10 mL) of benzylbromide (3.8 mL, 32 mmol). The reaction mixture is allowed to reach room temperature overnight and poured into a saturated NH4Cl aqueous solution. The aqueous layer is extracted twice with EtOAc and the combined organic extracts are dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica gel (hexane/EtOAc 97/3) to afford the title compound: TLC, Rf (hexane/AcOEt 95/5)=0.47; MS 249.9 [M+18].
Workup
- extractionThe aqueous layer is extracted twice with EtOAc
- dry with materialthe combined organic extracts are dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue is purified by flash column chromatography on silica gel (hexane/EtOAc 97/3)
Sources & evidence
- ORD record
- ord-45b9cee07ad1470399b0640d4dfbf640
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362040B2
Reaction notes
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