4-Nitrophenethyl alcohol → HCID 18765769, compound

Participants

Reaction Conditions

Reaction Steps

1.29 g (6.6 mmol) of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride, 0.92 ml (6.6 mmol) of Et3N and 1.62 ml (6.6 mmol) of tributylphosphine are added to a solution of 1.0 g (5.98 mmol) of 4-nitrophenethyl alcohol in 25 ml of CH2Cl2. The reaction mixture is agitated vigorously at 23° C. and 1.04 ml (6.6 mmol) of diethylazodicarboxylate is added dropwise. After 4 hours, the reaction is stopped by adding 5 ml of a saturated solution of NH4Cl. After decantation, the aqueous phase is extracted twice with 5 ml of CH2Cl2, the organic phases are combined and washed twice with 5 ml of water, twice with 5 ml of brine, dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is purified on a silica column (eluent Heptane/AcOEt: 9/1 to 7/3) in order to produce 1.20 g of the expected product.

Provenance & Evidence