Water → HCID 21243569, compound

HRID 621814Notes

Reaction equation

HRID 621814 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[OH:7][C:8]1[CH:12]=[C:11]([CH3:13])[O:10][C:9]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].BrC(C)C.O>CS(C)=O>[CH3:13][C:11]1[O:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([O:7][CH:2]([CH3:3])[CH3:1])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 23665647Potassium tert-butoxideHCID 54697152HCID 54697152, compound

Product 1

HCID 21243569HCID 21243569, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 1.6 g (14.3 mmol, 1.2 equiv) of potassium tert-butoxide in 11 mL of dimethyl sulfoxide is added to a solution of 2.0 g (11.8 mmol) of ethyl 3-hydroxy-5-methyl-2-furancarboxylate (Takei, H. and Mukaiyama, T., Bull. Soc. Chem. Jpn., 43, 3607 (1970)) in 40 mL of dimethyl sulfoxide under a nitrogen atmosphere. The resulting solution is stirred at room temperature for 1 hour and treated with 5.9 g (47.9 mmol, 4.1 equiv) of 2-bromopropane. The reaction is stirred at room temperature for 7.5 hours under nitrogen and poured onto 100 mL of water. The aqueous solution is extracted with ethyl acetate (4x). The combined extracts are washed with water (2x) and saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo to give 1.7 g (2.5 g theo., 68%) of ethyl 5-methyl-3-isopropoxy-2-furancarboxylate as a pale, yellow oil.

Workup

  1. stirringThe reaction is stirred at room temperature for 7.5 hours under nitrogen
  2. extractionThe aqueous solution is extracted with ethyl acetate (4x)
  3. washThe combined extracts are washed with water (2x) and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98d675ebfef149ba91c0a85005df149d
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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