Methanol → HCID 178487169, compound

HRID 1939301Notes

Reaction equation

HRID 1939301 reaction equation
[F:1][CH:2]([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].CO.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[CH2:21][CH2:20][CH2:19]2>CCOCC.Cl>[F:8][CH:2]([F:1])[C:3](=[C:21]1[CH2:20][CH2:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]([O:15][CH3:14])[CH:17]=2)[C:22]1=[O:26])[OH:5]

Participants

7

Reactant 4

HCID 887MethanolHCID 9961Ethyl difluoroacetateHCID 141126-Methoxy-alpha-tetraloneHCID 10942334Sodium Methoxide

Product 1

HCID 178487169HCID 178487169, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A 500 mL one neck round bottomed flask equipped with a nitrogen inlet and provisions for magnetic stirring was charged with ethyl difluoroacetate (6.2 g, 50 mmol) and 75 mL of ether. To this solution was added 12 mL of 25% sodium methoxide in methanol (52.5 mmol). A solution of 6-methoxy-1-tetralone (8.81 g, 50 mmol) in 125 mL of ether was added over about 1 minute. The reaction mixture was stirred at room temperature for 14 hours and was diluted with 150 mL of 1N HCl. The phases were separated and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was taken up in 70 mL of boiling ethanol/water and cooled to room temperature, whereupon crystals of 2-[2,2-difluoro-1-hydroxyethylidene]-3,4-dihydro-6-methoxy-1(2H)-naphthalenone (also known as 6-methoxy-2-difluoroacetyl-1-tetralone) formed which were isolated by filtration and air dried (10.8 g, 85%): mp 52°-54° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 14 hours
  2. customThe phases were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customformed which
  8. customwere isolated by filtration and air
  9. customdried (10.8 g, 85%)

Sources & evidence

ORD record
ord-73c89323e67a41e7b76464fe229ada4a
Source dataset
uspto-grants-1997_12
Patent number
US05696143

Reaction notes

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