Tetrahydrofuran → 7-Ethyl-beta-(phenylmethyl)-1H-indole-ethanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].COC(=O)C(CC1C=CC=CC=1)[C:11]1[C:19]2[C:14](=[C:15]([CH2:20][CH3:21])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH2:20]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[NH:13][C:12]([CH:32]([CH2:33][C:34]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1)[CH2:31][OH:30])=[CH:11]2)[CH3:21]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred suspension of lithium aluminum hydride (0.702 g, 18.5 mmol) in 80 mL of anhydrous tetrahydrofuran under nitrogen at 0° C. was slowly added (about 1.5 hours) a solution of 7-ethyl-α-(phenylmethyl)-1H-indole-3-acetic acid methyl ester (prepared in Step 2) (5.17 g, 16.8 mmol) in 30 mL of anhydrous tetrahydrofuran. The resulting dark red mixture was heated under reflux for 2 hours. It was cooled to 0° C., and quenched by the dropwise addition of 40 mL of water. The precipitated aluminum salts were removed by filtration and washed with ether. The layers of the filtrate were separated, and the aqueous layer was washed with ether. The combined ether layers were washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated to give the desired alcohol as a brown oil (4.51 g, 96%).
Workup
- temperatureThe resulting dark red mixture was heated
- temperatureunder reflux for 2 hours
- customquenched by the dropwise addition of 40 mL of water
- customThe precipitated aluminum salts were removed by filtration
- washwashed with ether
- customThe layers of the filtrate were separated
- washthe aqueous layer was washed with ether
- washThe combined ether layers were washed with saturated sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bf7c8b24bbdd464fb2e75cdc45c57574
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04670462
Reaction notes
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