Sodium Bicarbonate → 1172639-14-3

HRID 2076086Notes

Reaction equation

HRID 2076086 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[OH:16])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67095951HCID 67095951, compound

Product 1

HCID 200967681172639-14-3Yield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,4,5-trifluoro-phenyl)-cyclohexanol (215 mg, 0.93 mmol) dissolved in methylene chloride (15 mL) was added under nitrogen Dess-Martin reagent (475 mg, 1.1 mmol, 15 weight-percent in methylene chloride). The reaction was stirred at room temperature over night. The same amount of Des-Martin reagent was added and the reaction was stirred at room temperature over night. The reaction was poured onto a saturated sodium bicarbonate solution. The organic layer was washed with 10% aqueous sodium thiosulfate solution and brine, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was stirred with heptane/ethyl acetate (7:3 v/v) and the solid was filtered off to yield the title compound (202 mg, 95%) as a yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.10-7.20 (m, 2H), 3.84 (dd, 1H), 2.28-2.33 (m, 2H), 1.65-2.12 (m, 6H).

Workup

  1. additionwas added under nitrogen Dess-Martin reagent (475 mg, 1.1 mmol, 15 weight-percent in methylene chloride)
  2. additionThe same amount of Des-Martin reagent was added
  3. stirringthe reaction was stirred at room temperature over night
  4. washThe organic layer was washed with 10% aqueous sodium thiosulfate solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. stirringThe residue was stirred with heptane/ethyl acetate (7:3 v/v)
  9. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-59a900d994f444fb85aeac77f861b611
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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