Trifluoromethanesulfonate → HCID 20090591, compound

HRID 275182Notes

Reaction equation

HRID 275182 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[C:18]([CH:19]=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:36])([CH3:35])[C:25]=3[CH:24]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5])[CH3:2].[O-:37]S(C(F)(F)F)(=O)=O>>[CH2:1]([O:3][C:4]([CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[C:18]([C:19]([OH:37])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:35])([CH3:36])[C:25]=3[CH:24]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 2758875TrifluoromethanesulfonateHCID 20090587HCID 20090587, compound

Product 1

HCID 20090591HCID 20090591, compound

Procedure

3'-Ethoxycarbonylmethyl-2-(5,6,7,8-tetrahydro-5,5,8,8 -tetramethyl-2-naphthalenyl)methoxy-1,1'-biphenyl-6-carboxaldehyde (16q) (0.394 g., 0.84 mmol) obtained above (as a mixture with triflate 20a) is oxidized via the method of Example 4 to yield 3'ethoxycarbonylmethyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)methoxy-1,1'-biphenyl-6-carboxylic acid (0.210 g., 0.43 mmol, 25% overall from triflate 20a): chromatographed on silica gel using methanol/CH2Cl2 to afford a yellow oil; 1H NMR (300 MHz, CDCl3) δ 7.49 (d, J=8 Hz, 1H, ArH), 7.33 (m, 2H, ArH), 7.26-7.15 (m, 5H, ArH), 7.05 (d, J=2 Hz, 1H, ArH), 6.89 (dd, J=2, 8 Hz, 1H, ArH), 4.94 (s, 2H, ArCH2O), 4.05 (q, J=7Hz, 2H, CO2CH2), 3.59 (s, 2H, ArCH2CO2), 1.63 (s, 4H, CH2CH2), 1.22 (s, 6H, 2×CH3), 1.15 (s, 6H, 2×CH3), 1.15 (t, J=7 Hz, 3H, CO2CH2CH3); 13C NMR (75 MHz, CDCl3) δ 171.68 (C=O) , 171.64 (C=O), 156.21, 144.87, 144.23, 136.72, 133.58, 133.44, 132.16, 130.56, 128.42, 128.37, 128.01, 127.89, 126.55, 124.67, 123.89, 122.57, 116.76, 70.69, 60.80, 41.43, 35.03, 34.19, 34.07, 31.82, 31.74, 14.12; IR (film) 2960, 2926, 1734, 1700, 1456, 1364, 1300, 1260, 1152, 758 cm-1 ; MS (DCI) m/e 501 (MH+), 483 (M-OH), 201 (C15H21+).

Sources & evidence

ORD record
ord-3d751ab385794096aaae1f3d63392e2c
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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