Formaldehyde → HCID 18755538, compound

HRID 1861609Notes

Reaction equation

HRID 1861609 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[C:7]([CH2:16][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)=[O:5].[C:36](=O)([O-])[O-].[Na+].[Na+].C=O>C(Cl)(Cl)Cl.O>[CH:16]([C:7]1[N:8]=[C:9]([C:12]([F:13])([F:14])[F:15])[CH:10]=[CH:11][C:6]=1[C:4]([O:3][CH3:2])=[O:5])=[CH2:36]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 18755529HCID 18755529, compound

Product 1

HCID 18755538HCID 18755538, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

5.7 g (10 mmol) of (3-methoxycarbonyl-6-trifluoromethylpyridine-2-ylmethyl)triphenyl-phosphonium bromide are dissolved at room temperature in a 2-phase system of 25 ml of chloroform and 2.1 g (20 mmol) of sodium carbonate and reacted, in 10 ml of water, with a 35% aqueous solution of 1.7 g (20 mmol) of formaldehyde. After 1.5 hours, the organic phase is separated off and filtered through silica gel. Methyl 2-vinyl-6-trifluoromethylnicotinate is obtained as an oil, 1H-NMR (CDCl3): 8.31, d, CH, 7.10, dd, CH, 7.09, d, CH, 6.68, dd, CH, 5.68, dd, CH, 3.97 ppm, s, OCH3.

Workup

  1. customthe organic phase is separated off
  2. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-53c2288551584b0b8467a0b420779ba7
Source dataset
uspto-grants-2003_03
Patent number
US06534445B1

Reaction notes

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