Water → HCID 54488036, compound

HRID 1108768Notes

Reaction equation

HRID 1108768 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][C:11](=O)[CH2:10]2)=[CH:5][CH:4]=1.[Cl-].[CH3:16][O:17][CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].O>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][C:11](=[CH:16][O:17][CH3:18])[CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 140909103-(4-Methoxyphenyl)cyclopentan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 54488036HCID 54488036, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Methoxyphenyl)cyclopentanone (8.51 g) and methoxymethyltriphenylphosphonium chloride (16.9 g) were dissolved in tetrahydrofuran (200 ml). After gradually adding potassium tert-butoxide (6.70 g) while maintaining an internal temperature of 10° C. or below, the mixture was stirred at room temperature for 2.5 hours. The reaction solution was poured into water, and extraction with ethyl acetate was followed by washing with water. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to produce a brown oily substance which was then purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to give 4.73 g of 1-methoxy-4-(3-methoxymethylenecyclopentyl) benzene (48.4% yield).

Workup

  1. washby washing with water
  2. dry with materialAfter drying with anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto produce a brown oily substance which
  5. customwas then purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-781aa4627f2e42c38145a7a2825c7132
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

Loading…