Water → HCID 23117342, compound

HRID 131650Notes

Reaction equation

HRID 131650 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.N1C=CC=CC=1.[C:22]([C:25]1[S:29][C:28]2[C:30]3[C:35]([CH2:36][CH2:37][C:27]=2[CH:26]=1)=[CH:34][C:33](O)=[CH:32][CH:31]=3)(=[O:24])[CH3:23].O>C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>[C:22]([C:25]1[S:29][C:28]2[C:30]3[C:35]([CH2:36][CH2:37][C:27]=2[CH:26]=1)=[CH:34][C:33]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[CH:32][CH:31]=3)(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 23117349HCID 23117349, compound

Product 1

HCID 23117342HCID 23117342, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

5 mL of trifluoromethanesulfonic anhydride was added under ice cooling to a 50 mL pyridine solution of 5 g of the compound obtained in Example 39, and the system was stirred for 2 hours at the same temperature. After the reaction, water was added at the same temperature, and extraction was performed with ethyl acetate. The extracted organic layer was washed with saturated brine, dried with magnesium sulfate, and then subjected to reduced-pressure solvent distillation. The residue thus obtained was refined by silica gel column chromatography (25% ethyl acetate/hexane) to obtain 6.24 g of 2-acetyl-4,5-dihydro-7-(trifluoromethanesulfonyloxy)naphtho[1,2-b]thiophene in the form of a yellow powder.

Workup

  1. additionwas added at the same temperature, and extraction
  2. washThe extracted organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. distillationsubjected to reduced-pressure solvent distillation
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-8c312239f45b499e867b44b5ceb0fb4f
Source dataset
uspto-grants-2008_06
Patent number
US07384974B2

Reaction notes

Loading…