Sodium Bicarbonate → (1-benzylcyclopropyl)methanol

HRID 1809824Notes

Reaction equation

C([O:5][C:6]([C:8]1([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:11]([C:8]1([CH2:6][OH:5])[CH2:10][CH2:9]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -50 °C

Procedure

To a stirring solution of the title B compound, 1-benzyl-cyclopropanecarboxylic acid tert-butyl ester (0.232 g, 1 mmol) in THF (8 mL) under nitrogen is added drop wise at −50° C. LiAlH4 (3 mL, 3 mmol, 1 m in THF). The resulting mixture is further stirred for 1 h at −50° C., then slowly allowed to reach room temperature and poured into a saturated NaHCO3 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 4/1 to 1/1) to afford the title compound: TLC, Rf (hexane/AcOEt 1/1)=0.52. MS 180.0 [M+18]. Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 4.95 min.

Workup

customto reach room temperature
extractionThe aqueous layer is extracted twice with EtOAc
dry with materialand the 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 4/1 to 1/1)

Sources & evidence

ORD record: ord-0d9244f0c5634f89af59ff5eece66299
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362040B2

Reaction notes

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