(s)-(+)-5-[(1,1'-Biphenyl)-4-yl]-4-hydroxy-5-methyl-3-phenylmethoxy-2(5h)-furanone → (S)-(+)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone
Reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([C@:7]2([CH3:22])[O:11][C:10](=[O:12])[C:9]([O:13]CC3C=CC=CC=3)=[C:8]2[OH:21])=[CH:3][CH:2]=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:6]=[CH:5][C:4]([C@:7]2([CH3:22])[O:11][C:10](=[O:12])[C:9]([OH:13])=[C:8]2[OH:21])=[CH:3][CH:2]=1Participants
Procedure
The (S)-(+)-5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone was subjected to hydrogenation over 100 mg of 5% Pd/BaSO4 in 100 mL of MeOH at room temperature under 30 psi of H2. The reaction was monitored periodically by TLC analysis. Upon reaction completion, the suspension was filtered through two #1 filter papers, concentrated and recrystallized from CHCl3 and hexanes to provide 300 mg (20% overall yield from methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate) of (S)-(+)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone as a light weight white crystalline material: mp 204-206° C. dec.; [α]25D +121° (c=0.66; MeOH); 1H NMR (acetone-d6) δ 7.72-7.41 (m, 9H), 1.89 (s, 3H). Anal Calcd for C17H14O4 +0.75 H2O: C, 69.03; H, 5.28. Found: C, 68.69; H, 4.95.
Workup
- customUpon reaction completion
- filtrationthe suspension was filtered through two #1
- filtrationfilter papers
- concentrationconcentrated
- customrecrystallized from CHCl3 and hexanes
Sources & evidence
- ORD record
- ord-c85dd96d4c264e31a7ec7db8191c36f7
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06136832
Reaction notes
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