Phosphorus oxide (P4O10) → HCID 67100191, compound

HRID 1868898Notes

Reaction equation

O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2([C:29]([CH:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:32](OCC)=[O:33])=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:19]=[CH:20][C:21]=1[F:22]>OS(O)(=O)=O.C(OCC)C>[Cl:15][C:16]1[CH:17]=[C:18]2[C:19]([C:32]([OH:33])=[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:29](=[O:30])[C:23]32[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:20][C:21]=1[F:22]

Participants

Conditions

Temperature: 0 °C

Procedure

P2O5 (1.4 g) was suspended in H2SO4 (3.34 mL), and the mixture was cooled to 0° C. Diethyl 2-(4-(3-chloro-4-fluorophenyl)-tetrahydro-pyran-4-carbonyl)malonate (1.43 g, 3.57 mmol) was then added dropwise, and the resulting mixture was stirred for 1.5 hours. The reaction mixture was allowed to warm to ambient temperature and stirred for 5 hours. The reaction mixture was then poured into a beaker of ice, diluted with 200 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed with water (2×75 mL), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (0.96 g) as a colorless oil after flash chromatography. MS m/e=355 (M+H)+.

Workup

temperatureto warm to ambient temperature
stirringstirred for 5 hours
additionThe reaction mixture was then poured into a beaker of ice
additionadded to a separatory funnel
custompartitioned with water
washwashed with water (2×75 mL)
customseparated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c94766ac8b194e749e2a428ed4951625
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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