Benzyl Bromide → 2-Benzylcaprolactone
Reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.CN1C(=O)N(C)CCC1>[CH2:17]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:1]1=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
6
Procedure
A solution of 1 mmol of caprolactone in 0.5 mL THF was added to a solution of LDA in 0.5 mL THF at -78° C. and this stirred for 2 h. Then a solution of 1.1 mmol of a benzylbromide in 0.14 mL DMPU was added to the above mixture and after stirring for 1 h at -15° C., the 2-benzylcaprolactone was isolated by extraction and chromatography.
Workup
- stirringafter stirring for 1 h at -15° C.
Sources & evidence
- ORD record
- ord-1c2ee4b9716b4027b28c9669b15472c1
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05731432
Reaction notes
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