Triethyl phosphonoacetate → (E)-Ethyl 3-phenyl-3-(pyridazin-4-yl)acrylate

HRID 512194Notes

Reaction equation

C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[C:17]1([C:23]([C:25]2[CH:30]=[CH:29][N:28]=[N:27][CH:26]=2)=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[C:17]1(/[C:23](/[C:25]2[CH:30]=[CH:29][N:28]=[N:27][CH:26]=2)=[CH:9]\[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (1.46 g, 7.93 mmol) in THF (40 mL) was added NaH (476 mg, 11.9 mmol) in portions at 0° C., the resulting mixture was stirred at 0° C. for 20 minutes, then, the phenyl(pyridazin-4-yl)methanone was added in portions, the resulting mixture was stirred at 0° C. for 4 hour. The LC-MS showed the MS signal of desired product was detected, then, the reaction solution was added sat. aq. NH4Cl at 0° C., then, extracted with AcOEt (3×50 ml), the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to get the crude product, which was purified by column chromatography on silica gel (petroleum Ether: EtOAc=2:1) to afford (E)-ethyl 3-phenyl-3-(pyridazin-4-yl)acrylate (1.68 g, yield: 83.2%). 1H NMR (CDCl3 400 MHz): δ9.25 (d, J=5.2 Hz, 1H), 9.06 (s, 1H), 7.47-7.32 (m, 4H), 7.30-7.20 (m, 2H), 6.55 (s, 1H), 4.95 (q, J=7.2 Hz, 2H), 1.16 (t, J=7.2 Hz, 3H).

Workup

stirringthe resulting mixture was stirred at 0° C. for 4 hour

Sources & evidence

ORD record: ord-01ad819e168245fe8061e2d8391293b4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102591B2

Reaction notes

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