[(1R,2R)-2-phenylcyclopropyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1st stage: add a solution of 25.0 g (154 mmol) of trans-2-phenylcyclopropanecarboxylic acid in 100 ml of THF to a boron complex borane-THF solution drop by drop under a nitrogen atmosphere. Place the solution in the reflux for 3 hours and gently add 130 ml of NaOH 2N solution and stir the mixture for 30 minutes. Concentrate the etherised extracts in a vacuum to obtain 20.78 g of coarse trans-1-hydroxymethyl-2-phenylcyclopropane which is purified by distillation. reflux for 3 hours Concentrate the etherised extracts in a vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 104 mg of the alcohol was dissolved in 5 ml of chloroform and stirred with 445 mg of the Dess-Martin reagent (periodinane) at room temperature for 30 minutes. The reaction solution was poured into a mixture of saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1] to give 52 mg of the title compound as a colorless oily substance. extracted with ethyl acetate The organic layer was dried over anhydrous magnesium sulfate The desiccant was filtered off the solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1]

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 152 mg of lithium aluminium hydride suspended in 10 ml of tetrahydrofuran was mixed with 324 mg of trans-2-phenylcyclopropane-1-carboxylic acid under cooling with ice and stirred at the same temperature for 30 minutes and then at room temperature for 2 hours. Water was gradually added to the reaction solution and then 1N hydrochloric acid was gradually added. The reaction solution was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1→2/1] to give 307 mg of trans-l-(hydroxymethyl)-2-phenylcyclopropane as a colorless oily substance. under cooling with ice at room temperature for 2 hours The reaction solution was extracted with ethyl acetate the organic layer was dried over anhydrous magnesium sulfate The desiccant was filtered off the solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1→2/1]