Water → HCID 14993186, compound

HRID 486716Notes

Reaction equation

HRID 486716 reaction equation
Br[CH:2]([CH2:8][CH2:9][CH:10](Br)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]([O:5][CH2:6][CH3:7])=[O:4].O.O.O.O.O.O.O.O.O.[Na+].[Na+].[SH-:28].C(OCC)C.O>CN(C)C=O>[CH2:6]([O:5][C:3]([CH:2]1[CH2:8][CH2:9][CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:28]1)=[O:4])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 241588Diethyl 2,5-dibromohexanedioateHCID 162115161313-84-4

Product 1

HCID 14993186HCID 14993186, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of diethyl 2,5-dibromoadipate (4.5 g) in dimethylformamide (15 ml), sodium sulfide enneahydrate (3.9 g) was added under nitrogen atmosphere and the mixture was stirred for 5 hours under ice-cooling. To the reaction mixture, diethyl ether and water were added. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 2.1 g (72%) of 2,5-diethoxycarbonyltetrahydrothiophene.

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-6c4ea074ef4c4228a86f46b603155c44
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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