Sodium borohydride → 2-hydroxymethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 1281886Notes

Reaction equation

HRID 1281886 reaction equation
[CH:1]([C:3]1[S:17][C:6]2[O:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[CH:4]=1)=[O:2].[BH4-].[Na+]>CO.O>[OH:2][CH2:1][C:3]1[S:17][C:6]2[O:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 184221402-Formylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

Product 1

HCID 184221522-hydroxymethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Formylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.6 g) was suspended in methanol (30 ml) and sodium borohydride (480 mg) was added. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with water and extracted 3 times with chloroform. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. To the residue were added chloroform and diisopropyl ether and the precipitated crystals were collected by filtration to give 2-hydroxymethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.0 g).

Workup

  1. extractionextracted 3 times with chloroform
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the residue were added chloroform and diisopropyl ether
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-bbae3245b4314f84ae17d176b46eac19
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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