Sodium hydride → benzyl 2-(5-(4-bromophenyl)tetrahydro-2H-pyran-2-yl)acetate

HRID 515389Notes

Reaction equation

HRID 515389 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]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 123921660Benzyl 6-(4-bromophenyl)-7-hydroxyhept-2-enoate

Product 1

HCID 89872727benzyl 2-(5-(4-bromophenyl)tetrahydro-2H-pyran-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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).

Sources & evidence

ORD record
ord-99139afea21e4e9ab47f85e16f66d11e
Source dataset
uspto-grants-2015_08
Patent number
US09108956B2

Reaction notes

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