HCID 54374222, compound → HCID 54112197, compound
Reaction equation
[CH3:1][C@H:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2C2C=CC(C([O-])=O)=CC=2)=[CH:12][C:11]=1[N+:31]([O-:33])=[O:32])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C[C@H]([O:42]C1C=CC(OC(=O)C2C=CC=CC=2)=CC=1[N+]([O-])=O)CCCCCC>>[CH3:1][C@H:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:42])=[CH:18][CH:17]=2)=[CH:12][C:11]=1[N+:31]([O-:33])=[O:32])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
Procedure
The benzoyl ester of (S)-4'-(1-methylheptyloxy)-3'-nitro-4-biphenylylbenzoate was saponified using the same procedure as that used for saponification of (S)-[4-(1-methylheptyloxy)-3-nitrophenyl]-benzoate except that the reaction was carried out at 60° C. to give (S)-4'-(1-methylheptyloxy)-3'-nitro-4-hydroxybiphenyl (Compound 17, Scheme II, R2 =(S)-OCH(CH3)C6H13) as a very viscous orange liquid after flash chromatography with hexanes/ethyl acetate [88/12]; Rf [hexanes/ethyl acetate 85/15]: 0.17; 1H NMR (300 MHz, CDCl3): δ 0.86(t, 3H, J=6.6 Hz), 1.18-1.52(m, 8H), 1.35(d, 3H, J=6.1 Hz), 1.62(m, 1H), 1.78(m, 1H), 4.50(m, 1H), 5.22(broad s, 1H), 6.89(d, 2H, J=8.5 Hz), 7.07(d, 1H, J=8.8 Hz), 7.39(d, 2H, J=8.5 Hz), 7.62(dd, 1H, J=2.4 Hz, J=8.8 Hz), 7.92(d, 1H, J=2.4 Hz); 13C NMR (300 MHz, CDCl3): δ 13.99, 19.49, 22.50, 25.19, 29.10, 31.65, 36.17, 76.57, 115.94, 116.17, 123.30, 127.99, 131.21, 131.64, 133.09, 141.00, 15.42, 155.52; IR (CHCl2); 350, 3300(broad), 3020, 2920, 2840, 1610, 1540, 1510, 1485, 1350, 1260, 1220, 1160, 1110, 1040, 925, 825 cm-1 ; Mass spectrum, m/z(rel.intensity): 343(M+ 5), 231(100), 185(6), 57(6), 43(12).
Workup
- customwas carried out at 60° C.
Sources & evidence
- ORD record
- ord-089865359f524d09b8297b17963617f8
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05658493
Reaction notes
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