Water → HCID 23288042, compound

HRID 367298Notes

Reaction equation

C([O:4][C:5]1[C:6]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:7][C:8]2O[C:11]([CH2:14]I)([CH3:13])[CH2:10][C:9]=2[C:16]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=O)C.[C-:25]#[N:26].[K+].[OH2:28]>CS(C)=O>[C:17]([C:16]1[C:9]2[CH2:10][C:11]([CH2:13][C:25]#[N:26])([CH3:14])[O:28][C:8]=2[CH:7]=[C:6]([C:21]([CH3:22])([CH3:24])[CH3:23])[C:5]=1[OH:4])([CH3:19])([CH3:20])[CH3:18]

Participants

Conditions

Temperature: 140 °C

Procedure

In 5 ml of dimethyl sulfoxide were dissolved 1.00 g of 5-acetoxy-4,6-di-t-butyl-2-iodomethyl-2-methyl-2,3-dihydrobenzofuran synthesized in Example 70-2) and 0.36 g of potassium cyanide and the mixture was heated with stirring at 140° C. under nitrogen overnight. After cooling to room temperature, the reaction solution was poured into water and extracted with ether, and the combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography eluting with n-hexane containing 9-13% ethyl acetate to give 0.09 g of 4,6-di-t-butyl-2-cyanomethyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a colorless solid (yield 13%).

Workup

temperaturethe mixture was heated
temperatureAfter cooling to room temperature
extractionextracted with ether
washthe combined organic layers were washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography
washeluting with n-hexane containing 9-13% ethyl acetate

Sources & evidence

ORD record: ord-7901d497770d42ceb4d039c77b80cf2d
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133279

Reaction notes

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