Benzene → HCID 15078343, compound

HRID 1278265Notes

Reaction equation

HRID 1278265 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]2[C:13](=[O:19])[CH:14]=[C:15](C=O)[O:16][C:11]=2[C:10]=1[CH2:22][CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:27][CH2:28][CH3:29])=[O:26].[CH:50]1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]2[C:13](=[O:19])[CH:14]=[C:15](/[CH:50]=[CH:30]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[O:16][C:11]=2[C:10]=1[CH2:22][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 241Benzene2×HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 21163153HCID 21163153, compound

Product 1

HCID 15078343HCID 15078343, compound

Procedure

A solution of 7-benzyloxy-4-oxo-8-n-propyl-4H-1-benzopyran-2-carboxaldehyde (1.0 g) in dry benzene (30 ml) was added to a stirred solution of carbethoxymethylene-triphenylphosphorane (1.1 g) in dry benzene (50 ml). After 1 hour the solvent was evaporated and the remaining white solid was extracted several times with ether. The combined and concentrated ether washings were chromatographed over silica gel (100 g). Elution with ether afforded a white solid which was crystallised from ether to yield trans ethyl 3-(7-benzyloxy-4-oxo-8-n-propyl-4H-1-benzopyran-2-yl)acrylate (0.45 g) mp 140° C., a compound of the invention.

Workup

  1. customAfter 1 hour the solvent was evaporated
  2. extractionthe remaining white solid was extracted several times with ether
  3. customconcentrated ether washings were chromatographed over silica gel (100 g)
  4. washElution with ether
  5. customafforded a white solid which
  6. customwas crystallised from ether

Sources & evidence

ORD record
ord-6585c3f947004bf5a6604b99c50f87ab
Source dataset
uspto-grants-1981_07
Patent number
US04281008

Reaction notes

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