Hydrochloric Acid → HCID 57743111, compound

HRID 910140Notes

Reaction equation

HRID 910140 reaction equation
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=O.[S:13]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14]1.N12CCCN=C1CCCCC2.Cl.CN(C=[O:38])C>C(N(CC)CC)C.C(#N)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[C:2]([OH:38])([CH3:12])[O:20][C:19](=[O:21])[C:18]=2[C:15]2[CH:16]=[CH:17][S:13][CH:14]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 234043-Thiophenacetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Product 1

HCID 57743111HCID 57743111, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 3.08 g of 2-bromo-4′-chloropropiophenone, 1.79 g of 3-thiopheneacetic acid, acetonitrile and 10 ml of DMF was added 1.53 g of triethylamine, and the mixture was stirred for 2 hours at room temperature. The resultant mixture was cooled to 0° C., and 4.60 g of 1,8-diazabicyclo[5.4.0]undec-7-ene was added dropwise into this, and the mixture was stirred for 3 hours at room temperature. Then, the reaction mixture was stirred for 11 hours at room temperature while blowing air into the reaction mixture. To the reaction mixture was added 200 ml of 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and saturated brine sequentially, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure to obtain 3.98 g of 4-(4-chlorophenyl)-5-hydroxy-5-methyl-3-(3-thienyl)-2(5H)-furanone.

Workup

  1. stirringwas stirred for 3 hours at room temperature
  2. stirringThen, the reaction mixture was stirred for 11 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and saturated brine sequentially
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-451bb585a6304c83a094bf0a22adb07f
Source dataset
uspto-grants-2011_09
Patent number
US08022073B2

Reaction notes

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