Tetrahydrofuran → Di-tert-butyl 2,2'-(3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate

HRID 1486859Notes

Reaction equation

HRID 1486859 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH2:19][C:18]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[O:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C1COCC1>CO>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[CH2:19][C:18]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[O:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 118292732Di-tert-butyl 2,2'-(3-(3-(benzyloxy)phenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate

Product 1

HCID 118292806Di-tert-butyl 2,2'-(3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetateYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of di-tert-butyl 2,2′-(3-(3-(benzyloxy)phenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate (765 mg), a palladium carbon-ethylenediamine complex (38 mg), THF (10 mL), and methanol (10 mL) was stirred at room temperature for 30 hours under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (611 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d168d6ce72ab49e1b2a0914d5cad22a0
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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