Hydrochloric Acid → HCID 66841714, compound

HRID 391272Notes

Reaction equation

HRID 391272 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]2[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][O:9][C:8]=2[CH:15]=1.Cl.[CH3:17][O:18][C:19](=O)[O:20]C>>[CH3:17][O:18][C:19]([CH:12]1[CH2:11][CH2:10][O:9][C:8]2[CH:15]=[C:4]([F:3])[CH:5]=[CH:6][C:7]=2[C:13]1=[O:14])=[O:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl Carbonate2×HCID 24758Sodium hydrideHCID 146616228-Fluoro-2,3,4,5-tetrahydro-1-benzoxepin-5-one

Product 1

HCID 66841714HCID 66841714, compoundYield 7%

Procedure

A suspension of sodiumhydride in parrafin (0.49 g, 60%) was added to 5 ml dimethylcarbonate. To this suspension 8-Fluoro-3,4-dihydro-2H-benzo[b]oxepin-5-one (6.2 mmol) dissolved in 2 ml dimethylcarbonate was added dropwise at room temperature. The mixture was refluxed for two hours, cooled to room temperature and stirred overnight. 25 ml of 2 mol/l hydrochloric acid were added to the mixture. The resulting solution was extracted by ethyl acetate. The organic phase was dried over sodiumsulfate and the solvent removed in vacuo. The residue was dissolved in diethyl ether. 8-Fluoro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid methyl ester was obtained by crystallization from this solution in a yield of 7%. LC-MS: 1.8 min, 238.0 (MH+), 2.4 min, 238.0 (MH+)

Workup

  1. additionwas added dropwise at room temperature
  2. temperatureThe mixture was refluxed for two hours
  3. extractionThe resulting solution was extracted by ethyl acetate
  4. dry with materialThe organic phase was dried over sodiumsulfate
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was dissolved in diethyl ether

Sources & evidence

ORD record
ord-132e4b6f59304d52981cdc79ad60cfba
Source dataset
uspto-grants-2013_02
Patent number
US08383838B2

Reaction notes

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