Water → HCID 178472476, compound

HRID 1675333Notes

Reaction equation

[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1.[F:15][C:16]1[CH:21]=[C:20](F)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].O>CC(N(C)C)=O.C(OCC)(=O)C>[CH2:13]([O:12][C:10]([C@H:7]1[CH2:6][CH2:5][C@@H:4]([O:3][C:20]2[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([F:15])[CH:21]=2)[CH2:9][CH2:8]1)=[O:11])[CH3:14]

Participants

Conditions

Temperature: 4 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 5.05 g, 126 mmol) was added in one portion to a stirred solution of ethyl 4-hydroxycyclohexanecarboxylate (20.7 g, 120 mmol) and 2,4-difluoronitrobenzene (19.1 g, 120.2 mmol) in DMA (100 mL) at 4° C. and the mixture was stirred at 4° C. for 1 h and then the reaction mixture was warmed to ambient temperature and stirred for 24 h. The reaction mixture was cooled to 0° C. and then water and ethyl acetate were added. The layers were separated and the organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to leave a yellow oil. The oil was purified by column chromatography, using a gradient of 20-50% ethyl acetate in isohexane as eluent, to give the title compound as a pale yellow solid (4.1 g, 11%).

Workup

temperaturethe reaction mixture was warmed to ambient temperature
stirringstirred for 24 h
temperatureThe reaction mixture was cooled to 0° C.
customThe layers were separated
washthe organic layer was washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto leave a yellow oil
customThe oil was purified by column chromatography

Sources & evidence

ORD record: ord-17cd0c425b864c97a64f7e2ccf4742f8
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003676B2

Reaction notes

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