Reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22]Cl>CN(C=O)C.O>[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22][O:8][C:7]([C:6]1[CH:5]=[C:4]([CH3:10])[O:3][C:2]=1[CH3:1])=[O:9]Participants
Procedure
A 2 L round-bottomed flask equipped with a mechanical stirrer was charged with 2,5-dimethyl-3-furoic acid (81.0 g, 0.58 mol) and potassium carbonate (95.9 g, 0.69 mol) in DMF (500 mL). An ice bath was used to cool the reaction as 2-methoxyethoxymethyl chloride (72.2 g, 0.58 mol) was added portionwise. The reaction was stirred for 5 h at rt. The mixture was then diluted with water (1.5 L) and extracted with EtOAc (2×600 mL). The combined organics were washed with water (2×900 mL) and saturated sodium chloride solution (1 L), dried over MgSO4, filtered and concentrated to afford compound 803A (103 g, 82%) as a yellow oil. 1H NMR (CDCl3): δ=6.23 (s, 1H), 5.47 (s, 1H), 3.84 (m, 2H), 3.56 (m, 2H), 3.38 (s, 3H), 2.51 (s, 3H) and 2.20 ppm (s, 3H).
Workup
- customA 2 L round-bottomed flask equipped with a mechanical stirrer
- customAn ice bath was used
- temperatureto cool
- additionwas added portionwise
- extractionextracted with EtOAc (2×600 mL)
- washThe combined organics were washed with water (2×900 mL) and saturated sodium chloride solution (1 L)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3543461dbe844ff1830ab3cce5abf14d
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470797B2
Linked notes
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