Methyl formate → HCID 70131010, compound

HRID 1193866Notes

Reaction equation

HRID 1193866 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:19])[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=2)[CH:9]=[CH:8]1.[CH:20](OC)=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:21][CH:20]=[C:6]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=2)[CH:9]=[CH:8]1)[C:5]([O:4][CH3:3])=[O:19]

Participants

6

Reactant 4

HCID 7865Methyl formateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 21270674HCID 21270674, compound

Product 1

HCID 70131010HCID 70131010, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.58 g, 50% in oil, 12 mmol) was washed with petrol (60°-80° C.) and suspended in DMF (20 ml). To this, with vigorous stirring, was added dropwise, a solution of the crude methyl(6-ethoxyindol-1-yl)acetate (1.4 g, 6 mmol) and methyl formate (1.8 ml, 30 mmol) in DMF (10 ml) at room temperature. After 3 hours the reaction mixture was poured into 10% aqueous potassium carbonate (100 ml), washed with ether (2×100 ml), neutralised with concentrated hydrochloric acid and extracted with ether (2×100 ml). These extracts were washed with brine, dried and concentrated to give methyl 3-hydroxy-2-(6-ethoxyindol-1-yl)acrylate (1.0 g, 63% yield) as an orange oil.

Workup

  1. additionTo this, with vigorous stirring, was added dropwise
  2. customat room temperature
  3. washwashed with ether (2×100 ml), neutralised with concentrated hydrochloric acid
  4. extractionextracted with ether (2×100 ml)
  5. washThese extracts were washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bd97d2b4120549fca091d3245d347422
Source dataset
uspto-grants-1989_03
Patent number
US04812162

Reaction notes

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