Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 67794813, compound

HRID 2253729Notes

Reaction equation

HRID 2253729 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6]C=CC=1.[CH3:18][O:19][C:20](=[O:41])[CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:20]([CH:21]=[CH:13][C:12]1[CH:15]=[CH:16][C:9]([O:8][CH2:1][CH2:2][CH2:7][CH3:6])=[CH:10][C:11]=1[OH:17])([O:19][CH3:18])=[O:41]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 67794813HCID 67794813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzyloxy-2-hydroxybenzaldehyde (1.14 g, 5 mmol) and methyl(triphenylphosphoranylidene)acetate (3.51 g, 10 mmol) in THF (40 ml) is stirred at room temperature for 18 hours. The reaction mixture is then concentrated in vacuo and the residue purified by dry column chromatography using 25% EtOAc in hexane to 2:1/hexane:EtOAc. The concentrated residue is triturated with EtOAc/ether to obtain 2-carbomethoxyvinyl-5-butoxyphenol which is confirmed by NMR and used directly in the next step.

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo
  2. customthe residue purified
  3. customby dry column chromatography
  4. customThe concentrated residue is triturated with EtOAc/ether

Sources & evidence

ORD record
ord-4f389a972f8d4ba580cf71569029e313
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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