Sodium borohydride → HCID 19786582, compound

HRID 1657104Notes

Reaction equation

HRID 1657104 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[CH2:7][CH:8]1[C:22](=[O:23])[C:12]2[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][O:15][C:11]=2[CH2:10][CH2:9]1)C>C(O)C.[NH4+].[Cl-]>[OH:23][CH:22]1[C:12]2[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][O:15][C:11]=2[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][OH:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 53770206HCID 53770206, compound

Product 1

HCID 19786582HCID 19786582, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

In a 2 liter round-bottomed flask was dissolved 4,5,6,7-tetrahydro-4-oxo-3-phenyl-1,2-benzisoxazol-5-acetic acid ethyl ester (3.0 g) in absolute ethanol (300 ml) at room temperature. Sodium borohydride (6.07 g) was added and the solution was heated to reflux. The solution was cooled to room temperature, then diluted with saturated NH4Cl until a solid appeared. The reaction mixture was basified to pH 9 using 10% NAOH (aq.). The product, an oil, was extracted with ether and the aqueous phase was extracted twice with ether. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to give 2.60 g of 4-hydroxy-5-(2-hydroxyethyl)-3-phenyl-4,5,6,7-tetrahydro-1,2-benzisoxazole.

Workup

  1. temperaturethe solution was heated to reflux
  2. extractionThe product, an oil, was extracted with ether
  3. extractionthe aqueous phase was extracted twice with ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ee67cc65e5a74f9e8a4d304ab1e6c78a
Source dataset
uspto-grants-1993_10
Patent number
US05256672

Reaction notes

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