4-Hydroxybiphenyl → (2S)-2-(Biphenyl-4-yloxy)-3-methylbutyric acid, methyl ester
Reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][C@H:33]([CH:38]([CH3:40])[CH3:39])[C:34]([O:36][CH3:37])=[O:35].[C:41]1([C:47]2[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1>[C:41]1([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:46]=[CH:45][C:44]([O:32][C@@H:33]([CH:38]([CH3:40])[CH3:39])[C:34]([O:36][CH3:37])=[O:35])=[CH:43][CH:42]=1Participants
Procedure
Diethylazodicarboxylate (11.5 ml) in dry tetrahydrofuran (40 ml) was added dropwise over 30 minutes to a stirred solution of triphenylphosphine (22 g), methyl (R)-2-hydroxy-3-methylbutanoate (11.2 g, J.Am.Chem.Soc., (1990), 112, 21, 7659) and 4-phenylphenol (14.5 g) in dry tetrahydrofuran (120 ml). The resulting solution was stirred at room temperature overnight and was then concentrated under reduced pressure. A mixture of isohexane:ether (9:1) (750 ml) was added to the residue and the mixture stirred at room temperature for 30 minutes. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with isohexane:dichloromethane (1:4) then (1:1) to give the sub-title compound as a solid, which was recrystallised from hexane to give a crystalline solid (7.9 g).
Workup
- concentrationwas then concentrated under reduced pressure
- additionA mixture of isohexane:ether (9:1) (750 ml)
- additionwas added to the residue
- stirringthe mixture stirred at room temperature for 30 minutes
- filtrationThe solution was filtered
- concentrationthe filtrate concentrated under reduced pressure
- customThe residue was purified by column chromatography over silica eluting with isohexane:dichloromethane (1:4)
Sources & evidence
- ORD record
- ord-ac1e1952bb2c4d59ab92f68bea10a389
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300352B1
Reaction notes
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