Trifluoromethanesulfonic acid → HCID 67099727, compound

HRID 2078190Notes

Reaction equation

HRID 2078190 reaction equation
OS(C(F)(F)F)(=O)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:22]([CH:24]([C:30](OCC)=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1>CCOC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]2[C:13](=[CH:14][CH:15]=1)[C:16]1([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:22](=[O:23])[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:30]2[OH:31]

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 67099650HCID 67099650, compound

Product 1

HCID 67099727HCID 67099727, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triflic acid (40.4 mL) was added dropwise via addition funnel to diethyl 2-(1-(4-chlorophenyl)cyclohexanecarbonyl)malonate (17.65 g, 46.3 mmol) at 0° C. The resulting mixture was stirred for 1 hour and then poured into a beaker of ice. The resulting mixture was diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 2 times with 75 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (7.24 g) which was used without further purification. MS (m/z)=335 (M+H)+.

Workup

  1. additionpoured into a beaker of ice
  2. additionadded to a separatory funnel
  3. custompartitioned with water
  4. washwashed 2 times with 75 mL of NaHCO3 (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-373c283bf25b46808beadf28e8e883b4
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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