Sodium hydride → benzyl 2-(5-(4-bromophenyl)tetrahydro-2H-pyran-2-yl)acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:23][OH:24])[CH2:9][CH2:10][CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:4][CH:3]=1.[H-].[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:23][O:24][CH:11]([CH2:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of benzyl 6-(4-bromophenyl)-7-hydroxyhept-2-enoate (516 mg, 1.326 mmol) in dioxane (20 ml) at room temperature was added 60% NaH (106 mg, 2.65 mmol) and the mixture was stirred at 60° C. for 3 hr. Small amount of title compound was formed with the major SM. So the reaction was added more NaH and heated at 60° C. overnight. The reaction was quenched by sat. aq. NH4Cl and was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (5 to 100% Acetone/Heptane) to give the title compound 380 mg (yield 74%). MS (ESI) m/z 391.2 (M+2). Retention time 1.62 min (condition A).