1,2-Dimethoxyethane → HCID 23296058, compound
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[O:15][CH:16]1[C:21](=O)[CH2:20][CH2:19][O:18][CH2:17]1.[CH2:23](COC)OC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[O:15][CH:16]1[C:21](=[CH2:23])[CH2:20][CH2:19][O:18][CH2:17]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
18.2 g of methyltriphenylphosphonium bromide are suspended in 200 ml of dimethoxyethane under a nitrogen atmosphere and 1.5 g of sodium hydride (80% in paraffin) are then added in portions. The mixture is stirred at RT for 3 h and a solution of 13 g of methyl 4-methoxy-3-(4-oxotetrahydropyran-3-yloxy)benzoate are then added dropwise in the course of 30 min. The mixture is stirred overnight, then poured onto water and extracted 3 times with ethyl acetate. After drying over sodium sulfate, the organic phase is concentrated in vacuo and the residue is chromatographed on a silica gel column using ethyl acetate/petroleum ether 4:6. The chromatographically pure fractions are combined, concentrated and dried in a high vacuum. 3.6 g of the title compound are obtained as a pale yellow oil.
Workup
- stirringThe mixture is stirred overnight
- additionpoured onto water
- extractionextracted 3 times with ethyl acetate
- dry with materialAfter drying over sodium sulfate
- concentrationthe organic phase is concentrated in vacuo
- customthe residue is chromatographed on a silica gel column
- concentrationconcentrated
- customdried in a high vacuum
Sources & evidence
- ORD record
- ord-4d1d0fdf2f6f4358a49ad9dd9a061414
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121274
Reaction notes
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