Water → 4,6-Bismethoxymethoxy-5-prenyl-3-benzofuranone
Reaction equation
[CH3:1][O:2][CH2:3]Cl.[OH:5][C:6]1[C:11]2[C:12](=[O:15])[CH2:13][O:14][C:10]=2[CH:9]=[C:8]([OH:16])[C:7]=1[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20].[CH2:22](N(CC)CC)C.O.CN(C)[CH:32]=[O:33]>>[CH3:1][O:2][CH2:3][O:5][C:6]1[C:11]2[C:12](=[O:15])[CH2:13][O:14][C:10]=2[CH:9]=[C:8]([O:16][CH2:22][O:33][CH3:32])[C:7]=1[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20]Participants
Procedure
Chloromethyl methyl ether (0.4 ml, 5.27 mmol) was added dropwise to a stirred solution containing 4,6-dihydroxy-5-prenyl-3-benzofuranone (0.5 g, 2.14 mmol) and triethylamine (1 ml) in dimethylformamide (50 ml). After stirring at room temperature for 18 hours, water (100 ml) was added to destroy any excess chloromethyl methyl ether. The reaction mixture was extracted with ethyl acetate (2×250 ml), and the combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a light brown syrup. The crude mixture was chromatographed on silica gel, eluting with a mixture of ethyl acetate and hexanes (1:3), to give 4,6-bismethoxymethoxy-5-prenyl-3-benzofuranone (0.612 g, 88.8%) as a colorless powder.
Workup
- customto destroy any excess chloromethyl methyl ether
- extractionThe reaction mixture was extracted with ethyl acetate (2×250 ml)
- washthe combined organic extracts were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a light brown syrup
- customThe crude mixture was chromatographed on silica gel
- washeluting with a mixture of ethyl acetate and hexanes (1:3)
Sources & evidence
- ORD record
- ord-7032870c7d74481ca45cc42e625062ff
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06307070B1
Reaction notes
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