Hydrochloric Acid → HCID 67696855, compound

HRID 1755952Notes

Reaction equation

HRID 1755952 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]1[O:15][C:16]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](\[O:27][CH3:28])/[C:25]#[N:26])=[CH:19][C:17]=2[CH:18]=1.Cl.C[OH:31]>[OH-].[Na+]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][C:14]1[O:15][C:16]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](\[O:27][CH3:28])/[C:25]([NH2:26])=[O:31])=[CH:19][C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67696911HCID 67696911, compound

Product 1

HCID 67696855HCID 67696855, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of (Z)-3-[2-(5-methyl-2-phenyl-4-oxazolyl) methyl- 5-benzofuranyl]-2-methoxy-2-propenenitrile (0.10 g, 0.27 mmol) in methanol (10 ml) and sodium hydroxide (2 ml) was heated to reflux for 3 hours then cooled, acidified with 6N hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate and concentrated. The product was purified by flash chromatography (ethyl acetate/methanol/acetic acid, 75:1:1) and obtained as a solid (31 mg, m.p. 166°-169° C.).

Workup

  1. temperatureto reflux for 3 hours
  2. temperaturethen cooled
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (ethyl acetate/methanol/acetic acid, 75:1:1)

Sources & evidence

ORD record
ord-25c9c357b0ae4084ab70670f2a524ea2
Source dataset
uspto-grants-1995_08
Patent number
US05438074

Reaction notes

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