2-Methyl-2-butene → 3'-[4-(2-Tert-butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid

HRID 2422298Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:19][CH:18]=2)[CH:10]=1)=[O:2].P([O-])(O)(O)=[O:33].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(OCC)(=O)C.O1CCCC1.O.C(O)(C)(C)C>[C:28]([O:27][C:25]([CH2:24][CH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][C:11]2[CH:10]=[C:9]([C:4]3[C:3]([C:1]([OH:33])=[O:2])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:22][CH:21]=1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of tert-butyl 3-[4-(2′-formylbiphenyl-3-ylmethoxy)phenyl]propanoate (1.5 g, 3.60 mmol), sodium dihydrogenphosphate (0.43 g, 3.60 mmol), 2-methyl-2-butene (1.72 mL, 16.2 mmol), tert-butanol (7 mL), water (15 mL) and tetrahydrofuran (15 mL) was added sodium chlorite (1.22 g, 10.8 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 2 hrs. The reaction mixture was diluted with ethyl acetate, washed with water, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2) to give the title compound (1.12 g, 72%) as a yellow oil.

Workup

stirringthe mixture was stirred at the same temperature for 2 hrs
washwashed with water
dry with materialdried (anhydrous magnesium sulfate)
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/2)

Sources & evidence

ORD record: ord-8adb312d115b4365b5f9e93608722f26
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960369B2

Reaction notes

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