Hydrochloric Acid → HCID 21712727, compound

HRID 650601Notes

Reaction equation

HRID 650601 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:10][C:11]([CH:13]1[CH2:21][C:17]2[S:18][CH:19]=[CH:20][C:16]=2C(O)C1)=[O:12])[CH3:9].N1C=CC=CC=1.Cl>O.CCOC(C)=O>[C:5]([O:4][CH:1]1[C:16]2[CH:20]=[CH:19][S:18][C:17]=2[CH2:21][CH:13]([C:11]([O:10][CH2:8][CH3:9])=[O:12])[CH2:2]1)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21712788HCID 21712788, compound

Product 1

HCID 21712727HCID 21712727, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (4.1 ml) was added to a mixture of 6-ethoxycarbonyl-4-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene (2.06 g) and pyridine (8 ml) under water cooling, and was stirred at r.t. for 2.5 hours. The reaction mixture was added into a mixture of AcOEt and water, and was adjusted to pH 1.6 with 6N HCl. The separated organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate (sat. NaHCO3 aq.), water, and brine, and dried over MgSO4, and then evaporated in vacuo to give 4-acetoxy-6-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene (2.36 g) as an oil.

Workup

  1. washThe separated organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate (sat. NaHCO3 aq.), water, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-98e3f68ed53942ab965a7f2e0198ab0f
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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