Hydrochloric Acid → HCID 66840950, compound

HRID 391274Notes

Reaction equation

HRID 391274 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][O:10][C:9]=2[CH:16]=1)[CH3:4].Cl.[CH3:18][O:19][C:20](=O)[O:21]C>>[CH3:18][O:19][C:20]([CH:13]1[CH2:12][CH2:11][O:10][C:9]2[CH:16]=[C:5]([CH2:3][CH3:4])[CH:6]=[CH:7][C:8]=2[C:14]1=[O:15])=[O:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl Carbonate2×HCID 24758Sodium hydrideHCID 668412878-Ethyl-3,4-dihydro-1-benzoxepin-5(2H)-one

Product 1

HCID 66840950HCID 66840950, compoundYield 87%

Procedure

A suspension of sodiumhydride in paraffin (0.42 g, 60%) was added to 4 ml of dimethylcarbonate. To this suspension 8-Ethyl-3,4-dihydro-2H-benzo[b]oxepin-5-one (5.3 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. 8-Ethyl-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid methyl ester was obtained as a brown oil in a yield of 87%. LC-MS: 2.2 min, 249.0 (MH+), 2.7 min, 249.0 (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

Sources & evidence

ORD record
ord-aee71e18f2e24215b0d2f5d96e1c377f
Source dataset
uspto-grants-2013_02
Patent number
US08383838B2

Reaction notes

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