Water → HCID 14012545, compound

HRID 568693Notes

Reaction equation

HRID 568693 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][O:12][C:13]1[CH:28]=[CH:27][C:16]2[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[N:18][O:19][C:15]=2[C:14]=1[Cl:29])C.O.[OH-].[Na+]>CCOCC>[Cl:29][C:14]1[C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:16]=2[CH:27]=[CH:28][C:13]=1[O:12][CH2:11][CH2:10][OH:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13015713HCID 13015713, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14012545HCID 14012545, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 0.9 g lithium aluminum hydride (98%) in 100 ml anhydrous ether is added a solution of 10 g ethyl-2-{[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazole-6-yl]oxy}acetate of Example 1d in 200 ml ether containing sufficient tetrahydrofuran to effect solution. The reaction mixture is stirred for two hours at room temperature and one hour at reflux. To the reaction mixture is added 0.9 ml H2O, 0.9 ml 15% NaOH and 2.7 ml H2O. The stirred suspension is filtered and the filtrate is concentrated to afford 2-{[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazole-6-yl]oxy}ethanol, mp 112° C.

Workup

  1. temperatureat reflux
  2. filtrationThe stirred suspension is filtered
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-2fc2e5e63fe441e69b1977aaddd1617b
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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