Isopropanol → 2,5-Dimethyl-furan-3-carboxylic acid isopropyl ester

HRID 2110506Notes

Reaction equation

HRID 2110506 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[CH3:5][C:6]1[O:7][C:8]([CH3:14])=[CH:9][C:10]=1[C:11](Cl)=[O:12]>C(Cl)Cl>[CH:1]([O:4][C:11]([C:10]1[CH:9]=[C:8]([CH3:14])[O:7][C:6]=1[CH3:5])=[O:12])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 27348042,5-Dimethyl-3-furoyl Chloride

Product 1

HCID 598580682,5-Dimethyl-furan-3-carboxylic acid isopropyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropanol (5 ml) was added to a solution of 2,5-dimethylfuran-3-carbonylchloride (1.64 g; 10.3 mmol) in 15 ml of methylene chloride at rt. After allowing the reaction mixture to stand at rt for 30 mins, the volatiles were removed in vacuo and the residue was co-evaporated from isopropanol to afford compound 865A (1.8 g, 96%) as a light amber liquid. 1HNMR (CDCl3): δ 1.30 (d, j=6.5 Hz, 6H), 2.23 (s, 3H), 2.52 (s, 3H), 5.14 (m, 1H), 6.21 (s, 1H).

Workup

  1. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-9f4a335d6cb84d47a8cd6c74f72db718
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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