Triethyl phosphonoacetate → ethyl (5-fluoro-3,4-dihydro-2H-naphthalen-1-ylidene)acetate

HRID 331241Notes

Reaction equation

HRID 331241 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][CH2:22][C:23]2=O>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][CH2:22][C:23]2=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 86641631ethyl (5-fluoro-3,4-dihydro-2H-naphthalen-1-ylidene)acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of 60% sodium hydride (4.12 g) in toluene (200 ml) was added dropwise ethyl diethylphosphonoacetate (20.4 ml) under ice-cooling, and the mixture was stirred at room temperature for 45 min. Then, a solution of 5-fluoro-3,4-dihydro-2H-naphthalen-1-one (15.3 g) in toluene (50 ml) was added dropwise, and the mixture was stirred at 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was poured into ice water, and the mixture was extracted with toluene. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give ethyl (5-fluoro-3,4-dihydro-2H-naphthalen-1-ylidene)acetate.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 80° C. for 2 hr
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with toluene
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-71a0a324e50a4a0b909712235994d4e5
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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