Tetrahydrofuran → HCID 14986468, compound

HRID 654721Notes

Reaction equation

HRID 654721 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=CC=[CH:12][C:13]=2[CH3:15])[C:8]([CH:16]=O)=[CH:7][C:6]=1[CH:18]([CH3:20])[CH3:19])(=[O:3])[CH3:2].[C:21]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH2:24][CH3:25])=[O:22].O1CC[CH2:48][CH2:47]1>>[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:47][CH:48]=[CH:12][C:13]=2[CH3:15])[C:8](/[CH:16]=[CH:26]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]=1[CH:18]([CH3:19])[CH3:20])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 14986466HCID 14986466, compound

Product 1

HCID 14986468HCID 14986468, compound

Procedure

0.5 g of 4-acetoxy-3-isopropyl-5-methyl-1-naphthalenecarbaldehyde and 11 g of (carbethoxymethylene)triphenylphosphorane were dissolved in 50 ml of tetrahydrofuran and refluxed for 1 hour. The reaction mixture was cooled to room temperature and concetrated in vacuo. The resultant residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 0.5 g of the titled compound as pale yellow crystals.

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe resultant residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3619828173d54fb6954628b4ac52b5da
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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