Hydrochloric Acid → 3,3-difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine-6,8-dicarboxylic acid

HRID 1794557Notes

Reaction equation

HRID 1794557 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([C:18]([O:20]CC)=[O:19])=[C:9]2[C:15]=1[O:14][CH2:13][C:12]([F:17])([F:16])[CH2:11][O:10]2)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[F:17][C:12]1([F:16])[CH2:11][O:10][C:9]2=[C:8]([C:18]([OH:20])=[O:19])[S:7][C:6]([C:4]([OH:5])=[O:3])=[C:15]2[O:14][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 695461653,3-difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine-6,8-dicarboxylic acid diethyl ester

Product 1

HCID 222221443,3-difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine-6,8-dicarboxylic acidYield 71,571.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

953 mg (3.67 mmol) of 3,3-Difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine-6,8-dicarboxylic acid diethyl ester in 75 mL of ethanol was mixed with 1.10 g (27.5 mmol) of sodium hydroxide granules and stirred for 2 hours under nitrogen at room temperature. After acidifying the resulting mixture with 2N hydrochloric acid, the ethanol was largely evaporated off using a rotary evaporator, the solids filtered off, the filtrate washed three times with water and then dried in air. 736 g of 3,3-difluoro-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine-6,8-dicarboxylic acid was obtained corresponding to a yield of 92% yield with a melting point of 288–293° C., as characterized by:

Workup

  1. customthe ethanol was largely evaporated off
  2. customa rotary evaporator
  3. filtrationthe solids filtered off
  4. washthe filtrate washed three times with water
  5. customdried in air

Sources & evidence

ORD record
ord-ab0963cecf7949d4b8dab9acf926791e
Source dataset
uspto-grants-2006_04
Patent number
US07022811B2

Reaction notes

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