Benzyl Bromide → HCID 14642611, compound
Reaction equation
[H-].[Na+].[CH2:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].C(Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O1CCC[CH2:19]1>>[CH2:3]([O:9][CH:15]([CH3:14])[CH2:16][CH2:11][CH:12]=[CH2:13])[C:4]1[CH:19]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Procedure
To a stirred mixture of sodium hydride (2.6g, 110 mmoles) in tetrahydrofuran (185 ml) under a nitrogen atmosphere was added a solution of 5-hexene-1-ol (10g, 100 mmoles) in tetrahydrofuran (15 ml). After stirring at room temperature for 0.5 hour, the mixture was briefly heated to reflux and then cooled. Benzyl bromide (21.4 g, 125 mmoles) was added, and the mixture was stirred at reflux for one hour. Stirring was continued overnight at room temperature, after which the mixture was concentrated on a rotary evaporator. The mixture was poured into water, and the aqueous layer was extracted with three portions of ether. The combined organic extracts were dried over sodium sulfate, filtered, and the solvent evaporated. Chromatography of the residue on silica gel using a gradient of 0 to 10% ethyl acetate-hexane as eluant gave the title product (11.2 g) as an oil. The structure was confirmed by 1H NMR spectrometry.
Workup
- temperaturethe mixture was briefly heated
- temperatureto reflux
- temperaturecooled
- stirringthe mixture was stirred
- temperatureat reflux for one hour
- stirringStirring
- waitwas continued overnight at room temperature
- concentrationafter which the mixture was concentrated on a rotary evaporator
- additionThe mixture was poured into water
- extractionthe aqueous layer was extracted with three portions of ether
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-bc818d2ab3094185bec4999244036b84
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04973602
Reaction notes
Loading…