Water → HCID 24946152, compound

HRID 2383992Notes

Reaction equation

HRID 2383992 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]COC)=[C:15]([O:23][CH3:24])[CH:14]=3)=[C:10]([S:25][CH3:26])[C:9]=2[CH:27]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].O>ClCCl>[CH3:24][O:23][C:15]1[CH:14]=[C:13]([C:11]2[O:12][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][O:2][CH3:1])=[CH:27][C:9]=3[C:10]=2[S:25][CH3:26])[CH:18]=[CH:17][C:16]=1[OH:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 24946511HCID 24946511, compound

Product 1

HCID 24946152HCID 24946152, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The solution containing 590 mg of 5-(2-methoxy-ethyl)-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methylsulfanyl-benzofuran (14a; 1.52 mM) dissolved in 8 ml of dichloromethane was cooled to 0° C. 4.0 ml of trifluoroacetic acid was added thereto and stirred for 40 mins at 0° C. 7.5 g of solid sodium hydrogen carbonate and 60 ml of water were added thereto slowly at 0° C. The reaction mixture was extracted with dichloromethane. The organic solvent layer was dried with magnesium sulfuric acid, filtrated and the filtrate was concentrated with vaccuo.

Workup

  1. customslowly at 0° C
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. dry with materialThe organic solvent layer was dried with magnesium sulfuric acid
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated with vaccuo

Sources & evidence

ORD record
ord-98c46adc4c7d4622add427ea15ae16d6
Source dataset
uspto-grants-2012_09
Patent number
US08263649B2

Reaction notes

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