Sodium hydride → HCID 67006119, compound

HRID 564332Notes

Reaction equation

[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[F:14][C:15]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]2[C:16]=1[C:17]1([S:31]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[CH2:29][CH2:28][C:27](=O)[CH2:26][CH:18]1[CH2:19][O:20]2.[NH4+].[Cl-]>O1CCCC1>[F:14][C:15]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]2[C:16]=1[C:17]1([S:31]([C:34]3[CH:35]=[CH:36][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:38][CH:39]=3)(=[O:33])=[O:32])[CH2:29][CH2:28][C:27](=[CH:5][C:3]#[N:4])[CH2:26][CH:18]1[CH2:19][O:20]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. mixture of 60% NaH oil dispersion (60 mg) in tetrahydrofuran (11 mL) was added diethyl cyanomethylphosphonate (0.235 mL). After being stirred for 10 min at 0° C., 1,4-difluoro-10a-(4-trifluoromethyl-benzenesulfonyl)-6a,9,10,10a-tetrahydro-6H,7H-benzo[c]chromen-8-one (0.50 g, 1.12 mmol) was added to the resulting clear and colorless solution. After 1 h, saturated aqueous NH4Cl was added to the reaction solution. This mixture was then extracted with ethyl acetate (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The resulting crude residue (0.574 g) was used without further purification.

Workup

waitAfter 1 h
extractionThis mixture was then extracted with ethyl acetate (3×)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe resulting crude residue (0.574 g) was used without further purification

Sources & evidence

ORD record: ord-0347f02e22bb4cbebf225bea1870572c
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067621B2

Reaction notes

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