4-Hydroxybiphenyl → HCID 71354157, compound
Reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([O:37][CH2:38][CH3:39])(=[O:36])[C@H:33]([CH3:35])[OH:34].[C:40]1([C:46]2[CH:51]=[CH:50][C:49](O)=[CH:48][CH:47]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1>[C:40]1([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:45]=[CH:44][C:43]([O:34][C@H:33]([CH3:35])[C:32]([O:37][CH2:38][CH3:39])=[O:36])=[CH:42][CH:41]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Diethylazodicarboxylate (8.66 ml) in dry tetrahydrofuran (25 ml) was added dropwise over 30 minutes to a stirred solution of triphenylphosphine (13.11 g), (S)-(−)-ethyl lactate (5.67 ml) and 4-phenylphenol (8.51 g) in dry tetrahydrofuran (100 ml). The resulting solution was stirred at room temperature for 18 hours then concentrated under reduced pressure. A mixture of isohexane: ether (9:1) (200 ml) was added to the residue and 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 (2:3) to give the sub-title compound as an oil (11.79 g).
Workup
- concentrationthen concentrated under reduced pressure
- additionA mixture of isohexane: ether (9:1) (200 ml)
- additionwas added to the residue
- stirringstirred 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 (2:3)
Sources & evidence
- ORD record
- ord-3536590e28ba4cb09c50cf9576a31fc0
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300352B1
Reaction notes
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