Potassium Carbonate → 4-Chloro-6-methyl-11h-5-oxa-10-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1927528Notes

Reaction equation

HRID 1927528 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:28])[C:10]1[CH:15]=[C:14]([CH3:16])[C:13](Br)=[C:12]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=2[OH:27])[CH:11]=1>CN(C=O)C>[CH3:7][O:8][C:9]([C:10]1[CH:15]=[C:14]([CH3:16])[C:13]2[O:27][C:21]3[C:22]([Cl:26])=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][S:18][C:12]=2[CH:11]=1)=[O:28]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67246085HCID 67246085, compound

Product 1

HCID 672474734-Chloro-6-methyl-11h-5-oxa-10-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Anhydrous potassium carbonate (6.71 g, 48 mmol) was added to a solution of Example 154a (3.9 g, 9.7 mmol) in DMF (200 ml) and the reaction mixture was stirred at 80° C. for 4.5 h. It was concentrated and treated with ethyl acetate, then washed with 10% aqueous HCl, water, brine, dried, concentrated and purified using flash chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound as a white solid. Yield: 1.2 g (40%); 1H NMR (CDCl3): δ 2.64 (s, 3H, CH3), 3.88 (s, 3H, OCH3), 4.2 (s, 2H, CH2), 7.08 (m, 2H, Ar), 7.32 (q, 1H, Ar), 7.6 (s, 1H, Ar), 7.65 (s, 1H, Ar); MS: m/e (EI+) 320 (M+).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with ethyl acetate
  3. washwashed with 10% aqueous HCl, water, brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-eb9a5c1d0e4b413fac11bb8470d7263c
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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