Imidazole → HCID 86625642, compound
Reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:47]C1C=CC(CCCCCCCCCCCCCCCCCCO)=CC=1>C(Cl)Cl.C1C=CC=CC=1>[I:47][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 17-hydroxy-heptadecanoate 79 (264 mg, 0.84 mmol), Ph3P (262 mg, 1 mmol) and imidazole (94 mg, 1.39 mmol) were dissolved in the mixture of CH2Cl2 (3 ml) and benzene (3 ml) and cooled to 0° C. Solid 12 (254 mg, 1 mmol) was added and the reaction mixture was stirred at 0° C. for 40 min. The reaction mixture was quenched by addition of MeOH (0.5 ml), diluted with EtOAc and washed with the aqueous NaHCO3—Na2S2O3 solution, dried over Na2SO4 and evaporated. Chromatography in hexane-EtOAc (97:3) afforded the product 80 (321 mg, 90%).
Workup
- customThe reaction mixture was quenched by addition of MeOH (0.5 ml)
- additiondiluted with EtOAc
- washwashed with the aqueous NaHCO3—Na2S2O3 solution
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-4b8fe358cf8f479d9f84c425e6d4116d
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893286B2
Reaction notes
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