Trifluoroacetic acid → 5-(3-Ethoxypropyl)-3-iodo-5H-dibenzo[a,d]cycloheptene

Participants

Reaction Steps

5-(3-Ethoxypropyl)-3-iodo-5H-dibenzo[a,d]cyclohepten-5-ol (8.35 g., 0.020 mole) is mixed thoroughly with 7.6 g. (0.20 mole) of sodium borohydride and the mixture added carefully in portions to 130 ml. of trifluoroacetic acid stirred vigorously in an ice bath. A moderate stream of nitrogen is passed over the mixture throughout the addition, which is carried out in an efficient fume hood, and upon completion of the addition, the mixture is stirred for 15 minutes and concentrated in vacuo. The residue is treated with ice water, and the resulting gum separated by decantation. This residue is dissolved in toluene, extracted three times with 1 N NaOH, washed once with water, and dried over sodium sulfate. The solution is evaporated in vacuo to give the title compound as an orange oil.

Provenance & Evidence