Water → HCID 178472474, compound

HRID 660135Notes

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[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.O>CN(C=O)C.CCOC(C)=O>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:3][C@@H:4]2[CH2:5][CH2:6][C@H:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][CH2:9]2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 4.39 g, 109.7 mmol) was added in portions over 1 min to a stirred solution of ethyl 4-hydroxycyclohexanecarboxylate (18 g, 104.5 mmol) and 1-fluoro-4-nitrobenzene (11.1 mL, 109.7 mmol) in DMF (200 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 5 mins and then warmed to ambient temperature and stirred for 2 h. Water (750 mL) and EtOAc (300 mL) were then added and the layers were separated. The aqueous layer was extracted with EtOAc (2×300 mL) and the combined organic layers were washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo to leave a residue. The crude residue was purified by column chromatography, using a gradient of 10-40% EtOAc in isohexane as eluent, to give the title compound as a yellow oil (6.95 g, 23.7 mmol, 23%).

Workup

temperaturewarmed to ambient temperature
stirringstirred for 2 h
customthe layers were separated
extractionThe aqueous layer was extracted with EtOAc (2×300 mL)
washthe combined organic layers were washed with brine (100 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto leave a residue
customThe crude residue was purified by column chromatography

Sources & evidence

ORD record: ord-6ef12499380f4955a78f458dace23f6f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084478B2

Reaction notes

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