Hydrochloric Acid → 5-(2-Hydroxyethyl)-3,4-bis(4-methoxyphenyl)isoxazole

HRID 1608971Notes

Reaction equation

HRID 1608971 reaction equation
[BH4-].[Na+].C[O:4][C:5]([CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:9]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=O.Cl>CO>[OH:4][CH2:5][CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:9]=1[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 109262505-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl ester

Product 1

HCID 189989225-(2-Hydroxyethyl)-3,4-bis(4-methoxyphenyl)isoxazoleYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (5.9 g) was added to a suspension of 5 g of 5-methoxycarbonylmethyl-3,4-bis(4-methoxyphenyl)isoxazole in 20 ml of methanol, and the resulting mixture was stirred for 1 hour with ice cooling. The reaction mixture was made acidic by portionwise addition of 1N hydrochloric acid and then extracted with 80 ml of ethyl acetate. The extract was washed with 20 ml of 1N hydrochloric acid and 20 ml of water in that order, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4.5 g (yield 98%) of 5-(2-hydroxyethyl)-3,4-bis(4-methoxyphenyl)isoxazole.

Workup

  1. extractionextracted with 80 ml of ethyl acetate
  2. washThe extract was washed with 20 ml of 1N hydrochloric acid and 20 ml of water in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7efdd57d120147f8a087531226ced882
Source dataset
uspto-grants-1995_03
Patent number
US05399577

Reaction notes

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