Ethyl Acetate → HCID 86653760, compound

Participants

Reaction Steps

Dissolve 2.5 g (24.5 mmol) of cis/trans-cyclopentanediol in 5 ml of THF and, at 0° C., add 16.3 ml (16.3 mmol) of phosphazene base P4-t-Bu (approx. 1M solution in hexane). After 10 min, add the resulting solution dropwise to an ice-cooled solution of 4.77 g (24.5 mmol) of bromoacetic acid tert-butyl ester. After the end of the addition, warm to RT and stir the mixture overnight. Remove fractions of the THF under reduced pressure, dilute with ethyl acetate and wash successively with 1N hydrochloric acid, pH 7 buffer solution and satd. sodium chloride solution, dry over sodium sulphate and concentrate under reduced pressure. From the residue, isolate the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1→2:1). 631.4 mg (10.7% of theory) of the target compound are obtained as a cis/trans mixture.

Provenance & Evidence