Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-Biphenyl-4-yl-acrylic acid methyl ester

HRID 29690

Reaction equation

HRID 29690 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:15][O:16][C:17](=[O:38])[CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CC#N>[CH3:15][O:16][C:17](=[O:38])[CH:18]=[CH:7][C:4]1[CH:5]=[CH:6][C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Product 1

HCID 692086043-Biphenyl-4-yl-acrylic acid methyl esterYield 98.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-biphenylcarboxaldehyde (7.289 g, 40 mmol) in MeCN (80 ml) under nitrogen at room temperature was added methyl(triphenylphosphoranylidene)acetate (16.049 g, 48 mmol). After 18 h the reaction mixture was concentrated and the residue purified by flash chromatography, eluting with 10% EtOAc/hexane. The appropriate fractions were collected, filtered, concentrated and dried to give 3-biphenyl-4-yl-acrylic acid methyl ester (9.384 g, 39.38 mmol, 98%) as a pale yellow solid, mp 144-147° C. 1H NMR (DMSO-d6) δ 3.75 (s, 3H), 6.70 (d, 1H), 7.35-7.53 (m, 3H), 7.65-7.78 (m, 5H), 7.82 (d, 2H).

Workup

  1. concentrationAfter 18 h the reaction mixture was concentrated
  2. customthe residue purified by flash chromatography
  3. washeluting with 10% EtOAc/hexane
  4. customThe appropriate fractions were collected
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-140f6972872140b383ed35d93d174409
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Linked notes

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