Tetrahydrofuran → HCID 19858080, compound

HRID 2073400Notes

Reaction equation

HRID 2073400 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1.[F:14][C:15]([F:22])([F:21])[C:16](OCC)=[O:17].[H-].[Na+].O1CCCC1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:16](=[O:17])[C:15]([F:22])([F:21])[F:14])[C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 19858080HCID 19858080, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 7-methoxy-1-tetralone (7.8 g), ethyl trifluoroacetate (6 ml), sodium hydride (80% dispersion in mineral oil, 1.8 g) and tetrahydrofuran (75 ml) was stirred under reflux for 2 h under an atmosphere of argon. The cooled reaction mixture was treated with 20% acetic acid solution (250 ml) and the mixture was extracted twice with ethyl acetate. The extracts were combined, dried and evaporated to dryness under reduced pressure, and the residue was recrystallised from ethanol to give 7-methoxy-2-(2,2,2-trifluoracetyl)-1-tetralone, m.p. 89°-90°.

Workup

  1. temperatureunder reflux for 2 h under an atmosphere of argon
  2. customThe cooled reaction mixture
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-fa675a9cae654f56a2748de92936949e
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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