Benzyl Bromide → HCID 70048597, compound
Reaction equation
[CH2:1]([O:3][C:4]([CH2:6]/[CH:7]=[CH:8]/[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:5])[CH3:2].[Cl-].[Li+].[Li+].[CH3:18][CH:19]([N-]C(C)C)[CH3:20].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH2:33]1[CH2:37]O[CH2:35][CH2:34]1>>[CH2:13]([O:12][C:10](=[O:11])[CH:9]([CH2:35][C:34]1[CH:20]=[CH:19][CH:18]=[CH:37][CH:33]=1)[CH:8]=[CH:7][CH:6]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH3:14]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution 688 mg (3.44 mmol) trans-2-butene-1,4-dicarboxylic acid diethyl ester in 35 ml THF was added 1.46 g (34.4 mmol) anhydrous lithium chloride and the resulting suspension cooled to −78° C. 3.44 ml (6.88 mmol) of a 2 M solution of LDA in THF was added dropwise and stirring continued for 45 min. 0.82 ml (6.9 mmol) benzyl bromide was then added and stirring continued for 1 h at −78° C. and 10 min at 0° C. The reaction was quenched at this temperature by addition of saturated ammonium chloride solution and the mixture extracted three times with ether. The combined organic phases were washed with saturated brine, dried over sodium sulphate, and concentrated in vacuo. Flash chromatography (5% EtOAc in hexane) afforded 927 mg (71%) of the title compound as a yellow oil. MS m/e (%): 398 ([M+NH4]+, 100).
Workup
- stirringstirring
- waitcontinued for 1 h at −78° C. and 10 min at 0° C
- customThe reaction was quenched at this temperature by addition of saturated ammonium chloride solution
- extractionthe mixture extracted three times with ether
- washThe combined organic phases were washed with saturated brine
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-83229691c63048b1958bbbf1fbb0e27b
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262089B1
Reaction notes
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