Sodium borohydride → HCID 19786583, compound

HRID 1196588Notes

Reaction equation

HRID 1196588 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13](=[O:21])[CH:14]([CH2:17][CH2:18][CH2:19][Cl:20])[CH:15]=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]([OH:21])[CH:14]([CH2:17][CH2:18][CH2:19][Cl:20])[CH2:15][CH2:16][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19801312HCID 19801312, compound

Product 1

HCID 19786583HCID 19786583, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

In 100 ml of anhydrous THF was dissolved 6.0 g 3-(4-chlorophenyl)-5-(3-chloropropyl)-1,2-benzisoxazol-4(5H)-one under nitrogen atmosphere. The solution was cooled to -5° C. and 840 mg sodium borohydride was added. The reaction mixture was stirred at 0° C. for 45 minutes and then warmed to 10° C. for 20 minutes. After cooling to 0° C., the reaction mixture was quenched with aqueous NH4Cl (saturated) then extracted with ether. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 6.0 g of 3-(4-chlorophenyl)-5-(3-chloropropyl)-4-hydroxy-4,5,6,7-tetrahydro-1,2-benzisoxazole as an oil.

Workup

  1. temperaturewarmed to 10° C. for 20 minutes
  2. temperatureAfter cooling to 0° C.
  3. customthe reaction mixture was quenched with aqueous NH4Cl (saturated)
  4. extractionthen extracted with ether
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df13d7ba7fce4e58938130fab088b568
Source dataset
uspto-grants-1992_05
Patent number
US05114936

Reaction notes

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