Water → HCID 12429924, compound
Reaction equation
[C:1]([C:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][CH2:5][C:6](OCC)=[O:7])#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:2][CH2:1][C:3]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:4][CH2:5][CH2:6][OH:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of ethyl 4-cyano-4,4-diphenylbutyrate (1.2 g) in tetrahydrofuran (30 ml) was added lithium aluminum hydride (0.44 g) in small portion under ice-cooling. After completion of dropwise addition, the mixture was heated and stirred at 60° C. for 3 hours. The reaction mixture was then cooled with ice again, and water (1 ml), 15% aqueous sodium hydroxide (3 ml) and water (1 ml) were added in succession. The insoluble matter that had separated out was filtered off and the filtrate was extracted with ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic layer was taken, washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness. The group was washed with isopropyl ether to provide the title compound (0.82 g) as colorless powder.
Workup
- temperaturecooling
- additionAfter completion of dropwise addition
- temperaturethe mixture was heated
- temperatureThe reaction mixture was then cooled with ice again
- customThe insoluble matter that had separated out
- filtrationwas filtered off
- extractionthe filtrate was extracted with ethyl acetate and saturated aqueous sodium hydrogen carbonate
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated to dryness
- washThe group was washed with isopropyl ether
Sources & evidence
- ORD record
- ord-cc804ed094964e088cdc53d7d375a905
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05633248
Reaction notes
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