Sodium hydride → 2-(tetrahydro-4H-thiopyran-4-yloxy)nitrobenzene

HRID 476741Notes

Reaction equation

[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][S:7][CH2:6][CH2:5]1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]>O1CCOCC1>[S:7]1[CH2:8][CH2:9][CH:4]([O:3][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 90 °C

Procedure

To 50 ml of a dioxane suspension containing 0.96 g of 60% sodium hydride was added 3.6 g of 4-hydroxytetrahydrothiopyran at room temperature, and the mixture was stirred on heating at 90° C. with stirring for 6 hours. The temperature of the mixture was returned to room temperature, then 10 ml of a dioxane solution of 4.5 g of 2-fluoronitrobenzene was added dropwise, and the mixture was stirred overnight. The reaction solution was poured into ice water and extracted with ethyl ether, and the ethyl ether layer was washed, in turn, with water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated, and 1.1 g of the resulting oil was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=10:1 ) to give 6.1 g of 2-(tetrahydro-4H-thiopyran-4-yloxy)nitrobenzene as a pale yellow oil.

Workup

stirringwith stirring for 6 hours
customwas returned to room temperature
stirringthe mixture was stirred overnight
extractionextracted with ethyl ether
washthe ethyl ether layer was washed, in turn, with water
dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
customThe solvent was evaporated
custom1.1 g of the resulting oil was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=10:1 )

Sources & evidence

ORD record: ord-437a0276c13e4f47a14dd12e3e868b61
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885367

Reaction notes

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