1-Diethoxyphosphorylpropan-2-one → HCID 178467819, compound

HRID 500081Notes

Reaction equation

[H-].[Na+].[O:3]=[C:4]([CH3:14])[CH2:5]P(=O)(OCC)OCC.[CH:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]1)=O.[Cl-].[NH4+]>O1CCCC1>[O:3]=[C:4]([CH3:14])/[CH:5]=[CH:15]/[C@H:17]1[CH2:22][CH2:21][C@H:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of sodium hydride (793 mg) and anhydrous tetrahydrofuran (80 ml) under ice-cooling was added diethyl 2-oxopropylphosphonate (3.85 g). The mixture was stirred for 15 minutes and then a solution of t-butyl trans-4-formylcyclohexylcarbamate (3.00 g) in anhydrous tetrahydrofuran (30 ml) was added thereto. The mixture was warmed to 25° C. and stirred for 3 hours. To the reaction mixture was added saturated aqueous ammonium chloride, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 3.46 g of t-butyl trans-4-[(E)-3-oxo-1-butenyl]cyclohexylcarbamate.

Workup

temperaturecooling
stirringstirred for 3 hours
extractionthe mixture was extracted with ethyl acetate
washthe organic layer was washed with brine
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuo
customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

Sources & evidence

ORD record: ord-3f380f3234d2494db561c62d850dd285
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767854B2

Reaction notes

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