Methanol → HCID 68512797, compound

HRID 1808340Notes

Reaction equation

HRID 1808340 reaction equation
CSC.B.O=[C:6]1[CH2:11][O:10][C:9]2[CH:12]=[CH:13][C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:8]=2[NH:7]1.CO>C1COCC1>[O:10]1[CH2:11][CH2:6][NH:7][C:8]2[CH:15]=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:12][C:9]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 3785484Methyl (3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)acetateHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 68512797HCID 68512797, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane dimethylsulfide solution (0.3 ml, 94% in THF) was added at room temperature to a solution of the product from stage 1 (2.7 mmol) in dry THF (14 ml), and the mixture was refluxed for 2 h. Hydrolysis with methanol (1 ml) was carried out, followed by refluxing for a further 15 min. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/hexane). Yield: 62%

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. temperatureby refluxing for a further 15 min
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e0d2d3730e174c6a8adf6eb6b512b86a
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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