Water → HCID 54429164, compound

HRID 486720Notes

Reaction equation

HRID 486720 reaction equation
S(O[CH:6]([CH2:17][CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[CH2:7][C:8](=[CH2:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(C)(=O)=O.O.[SH-:27].[Na+].O>CN(C)C=O>[C:12]([O:11][C:9]([CH:8]1[CH2:16][S:27][CH:6]([CH2:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:7]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 16211346Sodium hydrosulfide hydrateHCID 53950019HCID 53950019, compound

Product 1

HCID 54429164HCID 54429164, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl 4-mesyloxy-2-methylene-6-tetrahydropyranyloxyhexanoate (1.38 g) in dimethylformamide (20 ml), sodium hydrosulfide hydrate (0.34 g) was added under nitrogen atmosphere and ice-cooling and the mixture was stirred for 7 hours. Water was added to the mixture and extracted with diethylether. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.67 g (58%) of 4-tert-butoxycarbonyl-2-(2-tetrahydropyranyloxyethyl)tetrahydrothiophene.

Workup

  1. temperatureice-cooling
  2. extractionextracted with diethylether
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-6a8ec0fe72bb4551a751609218a652ac
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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