HCID 135464263, compound → HCID 135432852, compound

HRID 466073Notes

Reaction equation

HRID 466073 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:22]2[NH:26][C:25](=[O:27])[O:24][N:23]=2)[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[O:11]COCCOC)([CH3:4])[CH3:3]>ClCCl.[Br-].[Zn+2].[Br-]>[CH3:21][C:18]([C:9]1[CH:8]=[C:7]([C:22]2[NH:26][C:25](=[O:27])[O:24][N:23]=2)[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:19])[CH3:20]

Participants

4

Reactant 1

HCID 135464263HCID 135464263, compound

Product 1

HCID 135432852HCID 135432852, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.9 g (0.005 mole) of 3-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-1,2,4-oxadiazol-5(4H)-one and 5.7 g (0.025 mole) of zinc bromide in dichloromethane (10 ml) is stirred vigorously at room temperature for three hours. The dichloromethane is then carefully decanted and the white solid is washed with additional dichloromethane (2×50 ml). The combined organic layers are washed with 10% sodium bicarbonate (2×50 ml), saturated sodium chloride (2×50 ml) and dried (anhydrous magnesium sulfate). Concentration leaves a solid which is recrystallized from ethyl acetate and hexane giving 0.7 g (48%) of 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,2,4-oxadiazol-5(4H)-one, mp 189°-191° C.

Workup

  1. customThe dichloromethane is then carefully decanted
  2. washthe white solid is washed with additional dichloromethane (2×50 ml)
  3. washThe combined organic layers are washed with 10% sodium bicarbonate (2×50 ml), saturated sodium chloride (2×50 ml)
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. concentrationConcentration
  6. customleaves a solid which
  7. customis recrystallized from ethyl acetate and hexane giving 0.7 g (48%) of 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,2,4-oxadiazol-5(4H)-one, mp 189°-191° C.

Sources & evidence

ORD record
ord-d5d0a28f99de4592b504816a7e005239
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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