Water → HCID 54218635, compound

HRID 328452Notes

Reaction equation

HRID 328452 reaction equation
[OH-].[Na+].[O:3]([N:5]=[C:6]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:7]([O:9]C)=[O:8])[CH3:4].O>CO>[CH3:4][O:3][N:5]=[C:6]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 53919049HCID 53919049, compound

Product 1

HCID 54218635HCID 54218635, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N-Sodium hydroxide (8.27 ml.) was added to a solution of methyl 2-methoxylimino-2-(thien-2-yl)-acetate (syn-isomer) (3.28 g.) in methanol (50 ml.) and the solution was stirred at room temperature for 18 hours. Water (20 ml.) was added and the solution was evaporated to remove methanol, and then washed with ethyl acetate. The pH of the solution under ethyl acetate (50 ml.) was altered to 2 with 2N-hydrochloric acid. The layers were separated and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried, and evaporated to a white solid (2.58 g.). This was crystallised from cyclohexane, producing the title compound (2.23 g., 73%), m.p. 105.5°, λmax.EtOH 289 nm (λ 10,100), λinf. 262 and 271 nm. (ε 7,750 and 8.150), τ (CDCl3) values include 0.32 (OH) and 5.92 (OCH3).

Workup

  1. customthe solution was evaporated
  2. customto remove methanol
  3. washwashed with ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. customdried
  7. customevaporated to a white solid (2.58 g.)
  8. customThis was crystallised from cyclohexane

Sources & evidence

ORD record
ord-407db0b9e8a745679f5477b4142d4cb1
Source dataset
uspto-grants-1977_04
Patent number
US04017515

Reaction notes

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