Sodium Bicarbonate → HCID 21712665, compound

HRID 650602Notes

Reaction equation

HRID 650602 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-dea4222385374e7dad089683be586e23
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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