Ethyl ketone → 1-(3-Benzyloxy-4-nitrophenyl)-2-methylpentan-3-one

HRID 660699Notes

Reaction equation

[CH3:1][CH2:2][C:3](=[O:6])[CH2:4][CH3:5].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:17]([O:24][C:25]1[CH:30]=[C:29]([CH2:31]Br)[CH:28]=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:17]([O:24][C:25]1[CH:30]=[C:29]([CH2:31][CH:2]([CH3:1])[C:3](=[O:6])[CH2:4][CH3:5])[CH:28]=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of pentan-3-one (516 mg, 6 mmol) in THF (5 mL) at −78° C. is added dropwise LiHMDS (6.6 mL of 1.0 M solution in THF, 6.6 mmol) over a period of 15 min. The solution is stirred at −78° C. for 2 h then a solution of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (Example 83, step C) (963 mg, 3 mmol) in THF (5 mL) is added dropwise. The mixture is allowed to warm to RT overnight and 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 10-50% EtOAc/hexane as eluent to give the title compound.

Workup

temperatureto warm to RT overnight
customis 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-57724db033ca4edd8955c692824c1807
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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