Methyl formate → HCID 67827060, compound

HRID 1742012Notes

Reaction equation

HRID 1742012 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, compoundYield 112.5%

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 (2.0 g) 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-dff4ec3923b044cea17b8148b24d3a0c
Source dataset
uspto-grants-1994_08
Patent number
US05336682

Reaction notes

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