Trifluoroacetic acid → HCID 57436857, compound

HRID 1723972Notes

Reaction equation

HRID 1723972 reaction equation
[C:1]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:22])[C:20]=2[CH3:21])=[C:17]([O:23]C(C)(C)C)[CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:22])[C:20]=2[CH3:21])=[C:17]([OH:23])[CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57436856HCID 57436856, compound

Product 1

HCID 57436857HCID 57436857, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round bottomed flask is charged with 2-(4-tertbutylbenzylmercapto)-3-methyl-5-tertbutoxy chromen-4-one (10 g, 24.3 mmol). To this is then added anhydrous trifluoroacetic acid (15 mL) and the reaction mixture is stirred for 8 hours at 0° C. Dichloromethane is then added to the flask and the mixture poured into a separatory funnel. It is then washed with water and then with brine and dried over sodium sulfate and filtered. The filtrate is then concentrated in vacuo and the residue obtained is purified by silica gel flash chromatography (ethyl acetate:hexanes) to obtain the desired product.

Workup

  1. additionthe mixture poured into a separatory funnel
  2. washIt is then washed with water
  3. dry with materialwith brine and dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is then concentrated in vacuo
  6. customthe residue obtained
  7. customis purified by silica gel flash chromatography (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-209d38966c7f41528227bf7a473dbfe0
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

Loading…