Propargyl bromide → 4-(2-Furyl)-4-methoxy-1-butyne
Reaction equation
[Br-].[CH2:2]([Al+2])[C:3]#[CH:4].[Br-].C(Br)C#C.[Al].CO[CH:14]([O:20][CH3:21])[C:15]1[O:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.O1CCCC1>[O:19]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:14]([O:20][CH3:21])[CH2:4][C:3]#[CH:2]Participants
7
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of propargyl aluminum bromide, prepared from 52.9 g of 80% propargyl bromide in toluene, 6.41 g of aluminum splutters activated with 70 mg of mercuric choride and 80 ml of tetrahydrofuran, was added dropwise a solution of 42.2 g of furfural dimethyl acetal [J. Org. Chem., 40, 1478 (1975)] in 30 ml of tetrahydrofuran during a 15 minute period while maintaining a temperature of. 25° to 30° C. The mixture was stirred for 20 minutes at 25° C., then partitioned with ether and ice-water. The organic layer was separated, washed with water, then aqueous sodium bicarbonate, finally with brine and dried. After evaporation the residue was distilled, giving 39.8 g of the desired compound, bp 68°-69° C. (11 mm).
Workup
- temperaturewhile maintaining a temperature of
- custom25° to 30° C
- custompartitioned with ether and ice-water
- customThe organic layer was separated
- washwashed with water
- dry with materialaqueous sodium bicarbonate, finally with brine and dried
- customAfter evaporation the residue
- distillationwas distilled
Sources & evidence
- ORD record
- ord-b993ba9142e94eea8bd5cbcb62f1af6c
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04958037
Reaction notes
Loading…