Pyridine → acetyl Sumiki's acid

HRID 612310Notes

Reaction equation

HRID 612310 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.ClCCl.N1C=CC=CC=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(OCC)(=O)C>[C:20]([O:1][CH2:2][C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 806425-(Hydroxymethyl)-2-furoic acid

Product 1

HCID 10330015acetyl Sumiki's acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-hydroxymethylfuran-2-carboxylic acid (5.90 g), dry dichloromethane (100 ml), pyridine (6.71 ml), 4-dimethyl-aminopyridine (507 mg), and acetic anhydride (4.21 ml) was stirred for 2 hours at room temperature. The mixture was diluted with ethyl acetate and washed with 5M hydrochloric acid and brine (3 times), dried (MgSO4), and evaporated. The residue was re-evaporated twice from dry toluene to give the title acid as a solid (5.00 g); δH [(CD3)2CO) 2.05 (3 H, s), 5.11 (2 H, s), 6.62 (1 H, d, J 4 Hz), 7.17 (1 H, d, J 4 Hz) and 8.31 (1 H, br s).

Workup

  1. washwashed with 5M hydrochloric acid and brine (3 times)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was re-evaporated twice from dry toluene

Sources & evidence

ORD record
ord-321e8bdff30a4a1099706f761e3f9458
Source dataset
uspto-grants-1999_12
Patent number
US06001997

Reaction notes

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