Water → HCID 14520333, compound
Reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH3:4].[C:7]1([C:13]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:14]2[CH:18]=[C:17]([CH:19]=[O:20])[N:16]=[CH:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[NH4+].O>O1CCCC1>[CH2:1]([CH:19]([C:17]1[N:16]=[CH:15][N:14]([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=1)[OH:20])[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- 20 °C
Procedure
A solution of 0.22 mole of n-butyl magnesium bromide in 75 ml of tetrahydrofuran is slowly added, under an atmosphere of argon, to 67.6 g (0.2 mole) of 1-triphenylmethyl-1H-imidazole-4-carboxaldehyde (obtained as described in 1.b. above) in 500 ml of tetrahydrofuran. The temperature of the mixture is maintained at about 20° C. by cooling on an ice-bath. When the addition is complete, stirring is maintained for 30 minutes at ambient temperature and then 11 g of ammonium chloride and 100 ml of water are successively added. The mixture is extracted with dichloromethane. The organic phases are dried over anhydrous sodium sulfate, then evaporated under reduced pressure. The residue is recrystallized from a 2:1 v/v ethyl acetate-diethyl ether mixture. 45.8 g of alpha-n-butyl-1-triphenylmethyl-1H-imidazole-4-methanol are obtained. Yield: 58% of theory; M.P.: 119°-120° C.
Workup
- temperatureby cooling on an ice-bath
- additionWhen the addition
- temperatureis maintained for 30 minutes at ambient temperature
- extractionThe mixture is extracted with dichloromethane
- dry with materialThe organic phases are dried over anhydrous sodium sulfate
- customevaporated under reduced pressure
- customThe residue is recrystallized from a 2:1 v/v ethyl acetate-diethyl ether mixture
Sources & evidence
- ORD record
- ord-7106cfe16f6c4a27b6f56ec0567e358e
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04814343
Reaction notes
Loading…