Methanol → HCID 19027583, compound

HRID 2256811Notes

Reaction equation

HRID 2256811 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([CH2:12][CH2:13][C:14](O)=[O:15])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>O1CCCC1>[C:1]1([C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][OH:15])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 6659683-(3-phenyl-1,2,4-oxadiazol-5-yl)propanoic acid

Product 1

HCID 19027583HCID 19027583, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.5 ml of borane-methyl sulfide complex in 2M solution in tetrahydrofuran, 920 mg of 3-(3-phenyl-1,2,4-oxadiazol 5-yl)-propanoic acid (prepared by SRIRASTAVA et al., J. Heterocycl. Chem., Vol. 21, p. 1193 (1984) and 20 ml of tetrahydrofuran was stirred for one hour at ambient temperature. 10 ml of methanol were added over 5 minutes and evaporation to dryness under reduced pressure was carried out. The residue was chromatographed on silica (eluant: ethyl acetate - hexane (6-4)) to obtain 485 mg of the expected product.

Workup

  1. customevaporation to dryness under reduced pressure
  2. customThe residue was chromatographed on silica (eluant: ethyl acetate - hexane (6-4))

Sources & evidence

ORD record
ord-d6a7c392a358417da35aeb7f62c06421
Source dataset
uspto-grants-1997_08
Patent number
US05656607

Reaction notes

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