Tetrahydrofuran → Methyl [2-(3,5-dimethoxyphenyl)cyclohexylidene]acetate

HRID 1632578Notes

Reaction equation

HRID 1632578 reaction equation
[H-].[Na+].O1CCC[CH2:4]1.C[C:9](P(OC)(O)=O)([C:11]([O-:13])=[O:12])[CH3:10].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:29]2C[CH2:33][CH2:32][CH2:31][C:30]2=O)[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1>O.C(O)(=O)C>[CH3:28][O:27][C:25]1[CH:24]=[C:23]([CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33][C:10]2=[CH:9][C:11]([O:13][CH3:4])=[O:12])[CH:22]=[C:21]([O:20][CH3:19])[CH:26]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 133666722-(3,5-Dimethoxyphenyl)cyclohexan-1-oneHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 54436910Methyl [2-(3,5-dimethoxyphenyl)cyclohexylidene]acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 3.9 g. (0.081 mole) 50% sodium hydride in 500 ml. anhydrous tetrahydrofuran (THF) was added dropwise at room temperature a solution of 16.2 g. (0.089 mole) trimethylphosphonoacetate in 50 ml. THF and the mixture stirred for 15 minutes. A solution of 17.4 g. (0.074 mole) 2-(3,5-dimethoxyphenyl)cyclohexanone in 100 ml. THF was added in portions after which the mixture was heated at 70° C. for three hours and cooled to 0° C. Glacial acetic acid, 5.4 g., was added and the resulting mixture diluted with water and extracted with ethyl acetate. The extracts were dried (Na2SO4) and evaporated to give 2 g. of crude product which was crystallized from isopropyl ether; 20.4 g., M.P. 80°-81° C. 1H--NMR (CDCl3) ppm (delta): 3.60 (s, 3H, COOCH3), 3.80 (s, 6H, OCH3), 5.20 (s, 1H, olefin), 6.34 (s, 3H, aromatic). Mass spectrum, exact mass for C17H24O4 : 292.3783. Found: 292.1658.

Workup

  1. additionTo a suspension of 3.9 g
  2. temperaturecooled to 0° C
  3. addition, was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extracts were dried (Na2SO4)
  6. customevaporated
  7. customto give 2 g
  8. customof crude product which was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-76fc34ff94cc40cfbef0a102a7ebb8b7
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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