Furfuryl Alcohol → (1RS,2SR,6RS,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-ene-3,5-dione
Reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[CH:17]1[C:21](=[O:22])[CH:20]=[CH:19][C:18]1=[O:23].[Mg+2].[I-].[I-]>>[OH:7][CH2:1][C:2]12[O:6][CH:5]([CH:4]=[CH:3]1)[CH:19]1[CH:20]2[C:21](=[O:22])[CH:17]([C:10]2[C:11]([CH3:16])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=2[CH3:8])[C:18]1=[O:23]Participants
4
Procedure
Furfuryl alcohol (4 ml, 46.7 mmol) is added to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (2.0 g, 9.3 mmol) and MgI2 (520 mg, 1.86 mmol) and the reaction is stirred for 17 hours. The reaction mixture is adsorbed onto silica gel and purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-ene-3,5-dione.
Workup
- custompurified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-1499e149ff694596b41c4a4955c9b88b
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754242B2
Reaction notes
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