Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 68784243, compound

HRID 2266026Notes

Reaction equation

HRID 2266026 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]([CH:12]=O)=[CH:10][CH:9]=[C:8]([C:14]([F:17])([F:16])[F:15])[N:7]=1.[CH3:18][O:19][C:20](=[O:41])[CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:18][O:19][C:20](=[O:41])[CH:21]=[CH:12][C:11]1[C:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[N:7][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86625537HCID 86625537, compound

Product 1

HCID 68784243HCID 68784243, compoundYield 80%

Procedure

N-Methoxy-2-(3-methoxy-propyl)-N-methyl-6-trifluoromethyl-nicotinamide (156 mg, 0.509 mmol) was reacted with 1M-LAH in THF solution to give 2-(3-methoxy-propyl)-6-trifluoromethyl-pyridine-3-carbaldehyde quantitatively as oil. The crude product was used directly in the following reaction. 2-(3-Methoxy-propyl)-6-trifluoromethyl-pyridine-3-carbaldehyde was reacted with methyl(triphenylphosphoranylidene)acetate (204 mg, 0.61 mmol) to give 3-[2-(3-methoxy-propyl)-6-trifluoromethyl-pyridin-3-yl]-acrylic acid methyl ester (124 mg, 80%).

Sources & evidence

ORD record
ord-7c0d711a1ecc401094adc43e81d54a6b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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