Dihydrobenzofuran → 4-(2,3-Dihydro-5-benzofuranyl)-4-oxo-2-trifluoroacetamidobutanoic acid

HRID 232095Notes

Reaction equation

HRID 232095 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C@@H:6]1[C:11](=[O:12])[O:10][C:8](=[O:9])[CH2:7]1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][CH2:20]1.[Cl-].[NH4+]>ClC(Cl)C>[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([C:8](=[O:9])[CH2:7][CH:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:14])[F:13])[C:11]([OH:12])=[O:10])=[CH:27][C:22]=2[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 10329DihydrobenzofuranHCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 12197622(S)-(-)-2-(Trifluoroacetamido)succinic anhydride

Product 1

HCID 143901514-(2,3-Dihydro-5-benzofuranyl)-4-oxo-2-trifluoroacetamidobutanoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

0.1 mole of the compound obtained in Example 1 and 0.05 mole of aluminum chloride suspended in 100 ml of dichloroethane are added to a solution of 12 ml of dichloroethane containing 0.05 mole of 2,3-dihydrobenzofuran. The mixture is stirred for 36 hours at room temperature and then hydrolyzed with saturated ammonium chloride solution. The mixture is extracted with dichloromethane and the extract washed with water, dried over magnesium sulfate, filtered and concentrated to obtain the expected product.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washthe extract washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a878a13015148bc9755d58af9685706
Source dataset
uspto-grants-1989_07
Patent number
US04851429

Reaction notes

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