Sodium Bicarbonate → HCID 21712665, compound

HRID 2289439Notes

Reaction equation

HRID 2289439 reaction equation
C(O[CH:5]1[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:8][CH:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:6]1)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14]([CH:7]1[CH2:8][C:9]2[S:10][CH:11]=[CH:12][C:13]=2[CH:5]=[CH:6]1)=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 21712727HCID 21712727, compound

Product 1

HCID 21712665HCID 21712665, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-acetoxy-6-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene (2.34 g), tosic acid monohydrate (0.13 g), and toluene (50 ml) was stirred at reflux for 2 hours. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and then the separated organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and brine, and dried over MgSO4, and then evaporated in vacuo. After evaporation of the filtrate, the resulting oil was purified by chromatography on silica gel (CHCl3 -MeOH as eluent) to give 6-ethoxycarbonyl-6,7-dihydrobenzo[b]thiophene (1.03 g) as an oil.

Workup

  1. temperatureat reflux for 2 hours
  2. washthe separated organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customAfter evaporation of the filtrate
  6. customthe resulting oil was purified by chromatography on silica gel (CHCl3 -MeOH as eluent)

Sources & evidence

ORD record
ord-1d3daeee01e74a7fae71964856276a7a
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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