Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14780584, compound

HRID 1650138Notes

Reaction equation

HRID 1650138 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[C:12]([CH:13]=O)=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:23][O:24][C:25]([CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:26]>ClCCl>[CH3:23][O:24][C:25](=[O:26])/[CH:27]=[CH:13]/[C:12]1[C:3]([N:2]([CH3:22])[CH3:1])=[N:4][C:5]2[C:10]([C:11]=1[C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14780583HCID 14780583, compound

Product 1

HCID 14780584HCID 14780584, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Dimethylamino)-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde (4.20 g) is dissolved in 100 ml of dichloromethane and (5.25 g, 1.1 equivalents) of methyl (triphenylphosphoranylidene) acetate is added in one portion. The reaction is stirred at room temperature for three days, evaporated, and the residue eluted through a 3-inch silica column to give 4.60 g of (E)-methyl-3-[2-(dimethylamino)-4-(4-fluorophenyl)-3-quinolinyl]-2-propenoate as an orange solid; 1H NMR (chloroform-d): δ 7.78-6.87 (m, 9H), 5.98 (d, 1H), 3.60 (s, 3H), 2.95 (s, 6H) ppm.

Workup

  1. customevaporated
  2. washthe residue eluted through a 3-inch silica column

Sources & evidence

ORD record
ord-4332eac01cda43c6a54a2c27bf07b3f9
Source dataset
uspto-grants-1990_05
Patent number
US04923861

Reaction notes

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