Trifluoroacetic acid → HCID 70065380, compound

HRID 2293695Notes

Reaction equation

HRID 2293695 reaction equation
[O:1]1[C:6](=[O:7])[CH:5]=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2.[CH:14]1([CH:17]([C:19]2[S:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[CH:23]=2)O)C[CH2:15]1.C(O)(C(F)(F)F)=[O:29]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:14]([CH:17]([C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH:23]=1)[C:5]1[C:6](=[O:7])[O:1][C:2]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:3]=2[C:4]=1[OH:29])[CH3:15]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21477088HCID 21477088, compoundHCID 178515731HCID 178515731, compound

Product 1

HCID 70065380HCID 70065380, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride solution of 2H-cycloocta[b]pyran-2-one of formula II-3 (196 mg) and cyclopropyl benzothien-2-yl carbinol of Preparation 65 (204 mg) is added several drops of TFA. The reaction is stirred for 30 minutes at room temperature without reaction. Several addition drops of TFA is added and the reaction stirred an additional 30 minutes. The solvent is removed in vacuo and the resulting solid dissolved in hot 40% EtOAc/hexane and placed in the freezer over night. The solid is collected on a filter to yield 257.5 mg of the title product.

Workup

  1. additionis added
  2. stirringthe reaction stirred an additional 30 minutes
  3. customThe solvent is removed in vacuo
  4. dissolutionthe resulting solid dissolved in hot 40% EtOAc/hexane
  5. waitplaced in the freezer over night
  6. customThe solid is collected on
  7. filtrationa filter

Sources & evidence

ORD record
ord-a99ab39b2a2f4c41b8ab056b7ce50f46
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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