Iodoethane → 2-(1-Ethoxyethyl)-3-benzyloxy-6-methyl-pyran-4(1H)-one
Reaction equation
CO[CH2:3][C:4]1OC(C)=CC(=O)C=1OCC1C=CC=CC=1.[OH:20][CH:21]([C:23]1[O:24][C:25]([CH3:38])=[CH:26][C:27](=[O:37])[C:28]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:22].ICC>>[CH2:3]([O:20][CH:21]([C:23]1[O:24][C:25]([CH3:38])=[CH:26][C:27](=[O:37])[C:28]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:22])[CH3:4]Participants
4
Procedure
In an analogous procedure in the preparation of 2-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one using 2-(1-hydroxyethyl)-3-benzyloxy-6-methyl-pyran-4(1 H)-one (5.2 g, 20 mmol, 1 eq.) and 9.36 g iodoethane (60 mmol, 3 eq.) yielded the title compound as an orange oil (5.4 g, 94% Crude). Further purification by column chromatography on silica gel (eluant: EtOAc) furnished the pure product as a bright yellow oil.
Sources & evidence
- ORD record
- ord-caf4442ceb994039a5a6b0303adf4c80
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06335353B1
Reaction notes
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