Potassium Acetate → HCID 19000639, compound

HRID 2260395Notes

Reaction equation

HRID 2260395 reaction equation
Br[CH2:2][C:3]1[CH:16]=[C:15]2[C:6]([C:7](=[O:18])[C:8]3[C:13]([C:14]2=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:5]2[CH2:19][CH2:20][CH2:21][C:4]=12.[C:22]([O-:25])(=[O:24])[CH3:23].[K+]>CN(C)C=O.ClCCl>[C:22]([O:25][CH2:2][C:3]1[CH:16]=[C:15]2[C:6]([C:7](=[O:18])[C:8]3[C:13]([C:14]2=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:5]2[CH2:19][CH2:20][CH2:21][C:4]=12)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 19000638HCID 19000638, compound

Product 1

HCID 19000639HCID 19000639, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dihydro-4-bromomethyl-1H-cyclopent[a]-anthracene-6,11-dione (173 mg, 0.51 mmol) in dimethylformamide (10 ml) is added anhydrous potassium acetate (200 mg) at 0° C. and stirred for 2.5 hours. The mixture is diluted with dichloromethane (50mL), washed with H2O, dried (Na2SO4), and evaporated in vacuo to dryness. The residue is chromatographed on a silica gel column (2×30 cm) using toluene/ethyl acetate (9:1 v/v) as the eluent. The main fraction is collected, evaporated, and the solid residue is recrystallized from EtOH to afford 4-acetoxymethyl-2,3-dihydro-1H-cyclopent[a]anthracene-6,11dione, 81 mg (50%), mp 160°-161° C. 1H NMR (CDCl3): δ2.18 (3H, s, Ac), 2.24 (2H, t, J=7.6 Hz, CH2 -2), 2.98 (2H, q, J=7.6 Hz, CH2 -3), 3.53 (2H, t, J=7.6 Hz, CH2 -1), 5.20 (2H, S, CH2 --OAc), 7.76-8.30 (5H, m, Ar--H). The product is used directly in the next step without further purification.

Workup

  1. washwashed with H2O
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo to dryness
  4. customThe residue is chromatographed on a silica gel column (2×30 cm)
  5. customThe main fraction is collected
  6. customevaporated
  7. customthe solid residue is recrystallized from EtOH

Sources & evidence

ORD record
ord-0b0a98a753994c4ca84061b7208deca4
Source dataset
uspto-grants-1995_12
Patent number
US05476952

Reaction notes

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