Trifluoroacetic acid → 5-(3-Ethoxypropyl)-3-iodo-5H-dibenzo[a,d]cycloheptene
Reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][C:7]1(O)[C:13]2[CH:14]=[C:15]([I:18])[CH:16]=[CH:17][C:12]=2[CH:11]=[CH:10][C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2)[CH3:2].[BH4-].[Na+].FC(F)(F)C(O)=O>>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][CH:7]1[C:13]2[CH:14]=[C:15]([I:18])[CH:16]=[CH:17][C:12]=2[CH:11]=[CH:10][C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2)[CH3:2]Participants
Procedure
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.
Workup
- additionA moderate stream of nitrogen is passed over the mixture throughout the addition, which
- additionupon completion of the addition
- concentrationconcentrated in vacuo
- additionThe residue is treated with ice water
- customthe resulting gum separated by decantation
- dissolutionThis residue is dissolved in toluene
- extractionextracted three times with 1 N NaOH
- washwashed once with water
- dry with materialdried over sodium sulfate
- customThe solution is evaporated in vacuo
Sources & evidence
- ORD record
- ord-4b8dc0c46ca94305aad37d16b61391ab
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04235820
Reaction notes
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