Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-ethyl 3-(3-(4-cyano-2-methylphenyl)-4-(4-methoxyphenyl)thiophen-2-yl)acrylate

HRID 536606Notes

Reaction equation

[CH:1]([C:3]1[S:4][CH:5]=[C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[CH3:16])=O.[C:25]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:27][CH2:28][CH3:29])=[O:26]>C1(C)C=CC=CC=1>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([C:7]2[C:6]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:5][S:4][C:3]=2/[CH:1]=[CH:30]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:9]([CH3:16])[CH:10]=1)#[N:13]

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of compound 4-(2-formyl-4-(4-methoxyphenyl)thiophen-3-yl)-3-methylbenzonitrile (Scheme I, 4A, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (0.16 g, 0.48 mmol) and (carbethoxymethylene)triphenylphosphorane (Ph3P═CHCOOEt) (0.17 g, 0.48 mmol) in toluene (15 mL) was heated to 100° C. for 14 h. After being cooled down to room temperature, the reaction mixture was concentrated and purified by silica gel column chromatography (petroleum ether/ethyl acetate=20:1) to afford (E)-ethyl 3-(3-(4-cyano-2-methylphenyl)-4-(4-methoxyphenyl)thiophen-2-yl)acrylate (Scheme I, 5A, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (0.27 g, yield 100%) as a white solid.

Workup

temperatureAfter being cooled down to room temperature
concentrationthe reaction mixture was concentrated
custompurified by silica gel column chromatography (petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record: ord-025e8f4ea3f3493aabee02c94eb9252c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859611B2

Reaction notes

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