HCID 22025443, compound → HCID 17966419, compound

HRID 733263Notes

Reaction equation

HRID 733263 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:10]=2)[C:5]1=[O:18]>O>[OH:13][CH:12]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([F:16])([F:17])[F:15])[CH:10]=2)[C:5](=[O:18])[N:4]1[CH2:3][C:2]([F:19])([F:1])[F:20]

Participants

3

Reactant 1

HCID 22025443HCID 22025443, compound

Product 1

HCID 17966419HCID 17966419, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5.5 g of 2-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-isoindole-1,3-dione were dissolved using 150 ml MeOH(anhydrous) and 1.0 g of KBH4 added at ambient temperature. The mixture was left at ambient temperature for 16 h, cooled to 0° C. and poured into 100 ml of water at 0° C. The methanol was removed in vacuo. The aqueous layer was extracted three times using 100 ml of CH2Cl2 each. The organic layer was dried over MgSO4 and the solvent was removed in vacuo to yield 4.2 g of a viscous oil (Rf(DIP)=0.37, MS (DCI): 300 (M+1)+).

Workup

  1. additionadded at ambient temperature
  2. customThe methanol was removed in vacuo
  3. extractionThe aqueous layer was extracted three times
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d4549f63d0a54be49b1ae45fba4c5f08
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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