Water → 2-Isopropoxy-6,7,8,9-Tetrahydro-5H-benzocyclohepten-9-one
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[CH:20](Br)([CH3:22])[CH3:21].O>CN(C=O)C>[CH:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:13]=1)([CH3:22])[CH3:21]Participants
6
Conditions
- Temperature
- 100 °C
Procedure
To a suspension of 2-hydroxy-6,7,8,9-Tetrahydro-5H-benzocyclohepten-9-one (9.69 g, 56.3 mmol) and potassium carbonate (23.3 g, 0.17 mol) in DMF (60 ml) was added dropwise, under ice-cooling, isopropyl bromide (34.6 g, 0.28 mol). The reaction mixture was stirred for one hour at 100° C., which was poured into water, followed by extraction of the organic substance with ethyl acetate. The extract solution was washed with brine and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=9:1) to give the above-titled compound (11.4 g, yield 93%, oil).
Workup
- additionwas added dropwise, under ice-
- temperaturecooling
- extractionfollowed by extraction of the organic substance with ethyl acetate
- washThe extract solution was washed with brine and water, which
- dry with materialwas dried over anhydrous magnesium sulfate
- distillationby distilling off the solvent
- customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=9:1)
Sources & evidence
- ORD record
- ord-ebbfab4b268341dda739dc4df3e4d4fa
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235789B1
Reaction notes
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