(2'-Methoxyethoxymethoxy-[1,1';3'1'']terphenyl-5'-yloxy)butane → 5'-Butoxy-[1,1';3',1'']terphenyl-2'-ol
Reaction equation
COCCOC[O:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:10][C:9]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.CCOC(C)=O.[Zn+2].[Br-].[Br-]>[CH2:21]([O:20][C:11]1[CH:12]=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]([OH:7])=[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:10]=1)[CH2:22][CH2:23][CH3:24]Participants
Procedure
To a stirred solution of (2′-methoxyethoxymethoxy-[1,1′;3′,1″]terphenyl-5′-yloxy)butane (0.237 g, 0.583 mmol) in CH2Cl2 (6 mL) at room temperature was added anhydrous ZnBr2 (0.656 g, 2.92 mmol). After 18 h at this temperature, the resulting mixture was diluted with EtOAc (100 mL). The organic layer was washed with sat. aq. NaHCO3 (10 mL) and brine (10 mL) and then dried (MgSO4). After concentration, the residue was purified by preparatory plate chromatography (10% EtOAc/petroleum ether) to afford the product (0.172 g, 92%) as a solid; 1H NMR (CDCl3) δ 0.97 (t, J=10.9 Hz, 3H), 1.39-1.60 (m, 2H), 1.68-1.87 (m, 2H), 3.97 (t, J=9.5 Hz, 2H), 5.05 (s, 1H), 6.87 (s, 2H), 7.32-7.62 (m, 10H); mass spectrum [(+) ESI], m/z 319 (M+H)+, 341 (M+Na)+.
Workup
- washThe organic layer was washed with sat. aq. NaHCO3 (10 mL) and brine (10 mL)
- dry with materialdried (MgSO4)
- concentrationAfter concentration
- customthe residue was purified by preparatory plate chromatography (10% EtOAc/petroleum ether)
Sources & evidence
- ORD record
- ord-205e71c89ad4437d91349ae9dc54abbb
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451827B2
Reaction notes
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