Trifluoroacetic acid → HCID 83261102, compound

HRID 1497019Notes

Reaction equation

HRID 1497019 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(O)(C(F)(F)F)=O.CCOC(C)=O>C(Cl)Cl>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 89862352HCID 89862352, compound

Product 1

HCID 83261102HCID 83261102, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 3B (1.00 g, 3.52 mmol) in DCM (5 mL) was added TFA (2.5 mL, 32. mmol). The reaction was stirred at rt for 2 h. The reaction mixture was concentrated and purified on a 24 g silica gel column eluted from 0 to 100% EtOAc in hexanes over 15 minutes to Intermediate 3C (650 mg, 2.71 mmol, 77.0% yield). LCMS=241 [M+1], RT=3.59 min (Method A).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on a 24 g silica gel column

Sources & evidence

ORD record
ord-47a30eb7027d4b088a67e33db6724edd
Source dataset
uspto-grants-2015_12
Patent number
US09199946B2

Reaction notes

Loading…