Water → HCID 70574310, compound

HRID 1389143Notes

Reaction equation

HRID 1389143 reaction equation
[H-].[Na+].[C:3](OCC)(=[O:5])[CH3:4].[C:9]([C:12]1[CH:21]=[C:20]([F:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=2)[CH:13]=1)(=[O:11])[CH3:10].O>C(COC)OC>[F:22][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=2)[CH:13]=[C:12]([C:9]([OH:11])=[CH:10][C:3](=[O:5])[CH3:4])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 12791517HCID 12791517, compound

Product 1

HCID 70574310HCID 70574310, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of sodium hydride (0.048 mol) and ethyl acetate (4.22 g, 0.048 mol) in dry dimethoxyethane (10 ml) under nitrogen, was treated over 30 minutes at room temperature with a solution of 2-acetyl-4-fluoro-6-methoxynaphthalene (5.33 g, 0.024 mol) in dry dimethoxyethane (25 ml). The reaction mixture was then stirred at 50° C. for 31/2 hours. After cooling it was treated with water (50 ml) then dilute hydrochloric acid (50 ml) and the orange precipitate collected by filtration, washed with petrol and dried. Recrystallisation from methanol/ether gave 3.2 g product m.p. 107°-8° C.

Workup

  1. temperatureAfter cooling it
  2. filtrationdilute hydrochloric acid (50 ml) and the orange precipitate collected by filtration
  3. washwashed with petrol
  4. customdried
  5. customRecrystallisation from methanol/ether

Sources & evidence

ORD record
ord-9764442a659d40c8aab5a1cfa7dc7a23
Source dataset
uspto-grants-1981_01
Patent number
US04243682

Reaction notes

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