Methyl formate → Methyl 3-hydroxy-2-(2-benzoylpyrrol-1-yl)acrylate

HRID 1742014Notes

Reaction equation

HRID 1742014 reaction equation
[H-].[Na+].[C:3]([C:11]1[N:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:14][CH:15]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:21](OC)=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:22][CH:21]=[C:16]([N:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:3](=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 7865Methyl formateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 6618880Methyl 2-(2-benzoylpyrrol-1-yl)acetate

Product 1

HCID 67826680Methyl 3-hydroxy-2-(2-benzoylpyrrol-1-yl)acrylateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (1.44 g, 55% in oil, 0.033 mol) was washed with petrol 60°-80° and suspended in DMF (15 ml). To this the methyl (2-benzoylpyrrol-1-yl)acetate (4.0 g, 0.0165 mol) in DMF (15 ml) and methyl formate (20.3 ml, 0.33 mol) was added dropwise at room temperature. After 4 hours it was poured into 200 ml of 10% potassium carbonate, washed with diethyl ether (2×100 mls), then the aqueous was neutralised with concentrated hydrochloric acid and extracted with diethyl ether (2×100 ml). These extracts were washed with brine, dried and evaporated to give methyl 3-hydroxy-2- (2-benzoylpyrrol-1-yl)acrylate (3.86 g, 86%) as a white crystalline solid melting at 112°-113°.

Workup

  1. washwashed with diethyl ether (2×100 mls)
  2. extractionextracted with diethyl ether (2×100 ml)
  3. washThese extracts were washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-1edaaa1dbdc349c3a391453245a91b54
Source dataset
uspto-grants-1994_08
Patent number
US05336682

Reaction notes

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