Sodium Chlorite → 3-Butoxy-4'-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic acid

HRID 2261864Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[N:23]([C:30]4[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:37])[N:24]=[CH:25][C:26]=3[CH:27]([CH3:29])[CH3:28])=[CH:16][C:15]=2[CH3:38])[CH:9]=[CH:10][C:11]=1[CH:12]=[O:13])[CH2:2][CH2:3][CH3:4].[O-:39]Cl=O.[Na+]>CC(O)(C)C.CC(=CC)C.O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[N:23]([C:30]4[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=4[Cl:36])[N:24]=[CH:25][C:26]=3[CH:27]([CH3:28])[CH3:29])=[CH:16][C:15]=2[CH3:38])[CH:9]=[CH:10][C:11]=1[C:12]([OH:39])=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-butoxy-4′-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2′-methyl-biphenyl-4-carbaldehyde (0.125 g, 0.227 mmol) in t-BuOH (2.0 mL) and 2-methyl-2-butene (1.0 mL) at 0° C. is treated with a solution of NaClO2 (205 mg, 2.27 mmol) and NaH2PO4—H2O (313 mg, 2.27 mmol) in water (2.0 mL). The mixture is stirred at 0° C. for 60 minutes. The organic layer is separated, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified using silica gel chromatography eluting with 50%-100% ethyl acetate in hexanes to give the title compound (0.120 g, 93%). ES/MS m/e 566.8; 568.7 (M+1).

Workup

customThe organic layer is separated
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue is purified
washeluting with 50%-100% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-0ffdff229d4144c998ffe413c19c7bb0
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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