Acetic Anhydride → HCID 18945439, compound

HRID 399827Notes

Reaction equation

HRID 399827 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18945167HCID 18945167, compound

Product 1

HCID 18945439HCID 18945439, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 3-hydroxymethyl-5-(pyrrol-1-yl)benzoate (4.0 g) in pyridine (40 ml) was added acetic anhydride (4.9 ml) under ice cooling. After being stirred for 3 hours under ice cooling, the reaction mixture was poured into ice-water and the product was extracted with diethyl ether. The diethyl ether extracts were washed with water, 1N-hydrochloric acid and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to afford methyl 3-acetoxymethyl-5-(pyrrol-1-yl)benzoate (4.68 g).

Workup

  1. extractionthe product was extracted with diethyl ether
  2. washThe diethyl ether extracts were washed with water, 1N-hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1)
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c84d4bc6d9c44379acd7557ceb89c5ed
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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