2-Methyl-2-butene → 4,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid
Reaction equation
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH:15]=[O:16])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]=1[O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])([CH3:4])([CH3:3])[CH3:2].P([O-])(O)(O)=[O:27].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:14])([C:15]([OH:27])=[O:16])[O:13][C:9]=2[CH:8]=[C:7]([C:17]([CH3:18])([CH3:20])[CH3:19])[C:6]=1[O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -5 °C
Procedure
To a solution of 0.5 g of 4,6-di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran in 5 ml of t-butyl alcohol were added 5 ml of a saturated aqueous sodium dihydrogenphosphate solution and 0.73 ml of 2-methyl-2-butene, and the mixture was cooled to -5° C. To this solution was added dropwise a solution of 0.14 g of sodium chlorite in 5 ml of distilled water, and the mixture was stirred for 20 minutes, then further stirred at room temperature for 15 minutes. The reaction solution was extracted with diethyl ether, and the combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was recrystallized from hexane to give 0.38 g of 4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid as a colorless powder (yield 73%).
Workup
- stirringfurther stirred at room temperature for 15 minutes
- extractionThe reaction solution was extracted with diethyl ether
- washthe combined organic layers were washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-823cd5f5eaa84674b78a37455a2d85c4
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06133279
Reaction notes
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