Methyl formate → HCID 67827060, compound

HRID 1534868Notes

Reaction equation

HRID 1534868 reaction equation
[H-].[Na+].[CH:3]([C:11]1[N:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:14][CH:15]=1)=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:21](OC)=[O:22].C(=O)(O)[O-].[Na+]>CN(C=O)C>[OH:22][CH:21]=[C:16]([N:12]1[CH:13]=[CH:14][CH:15]=[C:11]1/[CH:3]=[CH:4]/[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 54326898HCID 54326898, compound

Product 1

HCID 67827060HCID 67827060, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.63 g, 0.013 mol) was washed with petrol 60°-80° and suspended in DMF (30 ml) under nitrogen. To this methyl (2-styrylpyrrol-1-yl)acetate (1.6 g, 0.0066 mol) and methyl formate (8.2 ml, 0.13 mol) in DMF (10 ml) was added dropwise at room temperature. After 4 hours it was poured into 200 ml of saturated sodium bicarbonate, extracted with diethyl ether (2×100 ml), then the aqueous layer was neutralised with concentrated hydrochloric acid and extracted again with diethyl ether (2×100 ml). This was washed with brine, dried and evaporated to give methyl 3-hydroxy-2-[(E)-2-styrylpyrrol-1-yl]acrylate (2.Og) as an orange-yellow oil. This was used in the following reaction without further purification.

Workup

  1. extractionextracted with diethyl ether (2×100 ml)
  2. extractionextracted again with diethyl ether (2×100 ml)
  3. washThis was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6d079191297644b49c032fbb51eedac9
Source dataset
uspto-grants-1992_02
Patent number
US05091407

Reaction notes

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