Glycol monoethyl ether → HCID 58903181, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=3)[CH:10]=2)=[C:4]([CH3:29])[CH:3]=1.[CH2:30]([O:32][CH2:33][CH2:34]O)[CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:30]([O:32][CH2:33][CH2:34][O:1][C:2]1[CH:3]=[C:4]([CH3:29])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=3)[CH:10]=2)=[C:6]([CH3:8])[CH:7]=1)[CH3:31]Participants
6
Procedure
To a solution of methyl 3-[4-[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl]propanoate (0.20 g, 0.51 mmol), 2-ethoxyethanol (0.099 mL, 1.02 mmol) and triphenylphosphine (0.18 g, 0.67 mmol) in tetrahydrofuran (4.0 mL) was added dropwise diethyl azodicarboxylate (40% toluene solution, 0.30 mL) at 0° C. with stirring and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1) to give the title compound (0.12 g, yield 51%) as a colorless oil.
Workup
- stirringthe mixture was stirred at room temperature for 12 hrs
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1)
Sources & evidence
- ORD record
- ord-8f227f099d6c421d92aacf2c54e690e0
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456218B2
Reaction notes
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