Butyrophenone → 2-(3-Benzyloxy-4-nitrobenzyl)-1-phenylbutan-1-one

HRID 660703

Reaction equation

[C:1]1([C:7](=[O:11])[CH2:8][CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([CH2:36]Br)[CH:33]=[CH:32][C:31]=1[N+:38]([O-:40])=[O:39])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([CH:33]=[CH:32][C:31]=1[N+:38]([O-:40])=[O:39])[CH2:36][CH:8]([CH2:9][CH3:10])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-phenylbutan-1-one (203 mg, 1.37 mmol) in THF (2.5 mL) at −78° C. is added dropwise LiHMDS (1.62 mL of 1.0 M solution in THF, 1.62 mmol) over a period of 15 min. The solution is stirred at −78° C. for 1 h then a solution of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (Example 83, step C) (400 mg, 1.25 mmol) in THF (2.5 mL) is added dropwise. The mixture is allowed to warm to RT and stirred there for 1 h then is quenched with saturated ammonium chloride solution. The mixture is extracted with EtOAc and the organic phase is washed with brine then dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of 5-100% EtOAc/hexane as eluent to give the title compound.

Workup

temperatureto warm to RT
stirringstirred there for 1 h
customthen is quenched with saturated ammonium chloride solution
extractionThe mixture is extracted with EtOAc
washthe organic phase is washed with brine
dry with materialthen dried over magnesium sulfate
customThe solvent is removed under reduced pressure
customthe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-8d07e62cd094468fb85af82de7512bca
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Linked notes

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