5-Methylfurfural → HCID 67485532, compound

HRID 2233363Notes

Reaction equation

HRID 2233363 reaction equation
[CH3:1][O:2][C:3]([CH:5]([PH4])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4].[CH3:15][C:16]1[O:20][C:19]([CH:21]=O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[C:10]([O:9][C:7](=[O:8])[CH2:6]/[C:5](/[C:3]([O:2][CH3:1])=[O:4])=[CH:21]\[C:19]1[O:20][C:16]([CH3:15])=[CH:17][CH:18]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 120975-MethylfurfuralHCID 178501885HCID 178501885, compound

Product 1

HCID 67485532HCID 67485532, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-methoxycarbonyl-2-t-butoxycarbonyl ethyl phosphorane (JCS Perkin II, 1975, p1030; 2.69 g, 6 mmol, 1.2 eq) and 5-methylfuran-2-al (0.5 ml, 5 mmol) in dry toluene (10 ml) was stirred at 80° C. for 48 hrs, and then evaporated to dryness. The residue was chromatographed (50 g Bondelut, eluting with hexane containing 10% v/v ethyl acetate) to yield the title compound as a brown oil (1.39 g, 100%). NMR: 1.38 (s, 9H), 2.33 (s, 3H), 3.62 (s, 2H), 3.71 (s, 3H), 6.31 (d, 1H), 6.85 (d, 1H), 7.42 (s, 1H).

Workup

  1. customevaporated to dryness
  2. customThe residue was chromatographed (50 g Bondelut
  3. washeluting with hexane containing 10% v/v ethyl acetate)

Sources & evidence

ORD record
ord-94809b9cb0fa4fd7bd7bc28849456598
Source dataset
uspto-grants-2010_05
Patent number
US07709505B2

Reaction notes

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