Hydrochloric Acid → HCID 22990006, compound

HRID 1169314Notes

Reaction equation

HRID 1169314 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][C:13]=3[CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+].Cl>C1COCC1>[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=3[CH:23]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 22990210HCID 22990210, compound

Product 1

HCID 22990006HCID 22990006, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl 7-phenylethynyl-2,3-dihydro-1-benzooxepine-4-carboxylate (463 mg, 1.52 mmol) were added methanol (10 ml), THF (10 ml) and a 1 N aqueous solution of sodium hydroxide (4.56 ml), and the resulting mixture was stirred at room temperature for 24 hours. After addition of 1 N hydrochloric acid (4.56 ml), the reaction mixture was concentrated under reduced pressure and was mixed with water, and an insoluble material was collected by filtration. The insoluble material was successively washed with water and diisopropyl ether, and was then dried under reduced pressure to obtain 7-phenylethynyl-2,3-dihydro-1-benzooxepine-4-carboxylic acid (417 mg, 1.44 mmol, 94%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionwas mixed with water
  3. filtrationan insoluble material was collected by filtration
  4. washThe insoluble material was successively washed with water and diisopropyl ether
  5. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-4f73b1dc44a04441a87cde0ee30e20dc
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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