Trifluoroacetic acid → HCID 178444318, compound

HRID 254121Notes

Reaction equation

HRID 254121 reaction equation
FC(F)(F)C(O)=O.[CH3:8][CH:9]([CH2:17][CH2:18][CH:19]([OH:31])[C@H:20]1[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:21]1)[C:10]([O:12]C(C)(C)C)=O>ClCCl.O>[CH3:8][CH:9]1[CH2:17][CH2:18][CH:19]([C@H:20]2[CH2:21][CH2:22][C@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25]2)[O:31][C:10]1=[O:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178444540HCID 178444540, compound

Product 1

HCID 178444318HCID 178444318, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14.2 mL (185 mmol) of trifluoroacetic acid dissolved in 60 mL of dichloromethane was added dropwise under cooling with ice to a solution of 12.6 g (37.0 mmol) of tert-butyl 2-methyl-5-hydroxy-5-(trans-4-pentylcyclohexyl)pentanoate (36) obtained in the first step dissolved in 60 mL of dichloromethane, and reacted at room temperature for 5 hours. The reaction mixture was put in 200 mL of water, and then extracted with 100 mL of dichloromethane. The resulting organic layer was washed with water (150 mL×2) and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (developing solvent: heptane/ethyl acetate=9/1, column packing: silica gel) and then recrystallized from heptane to obtain 3.7 g (13.7 mmol) of 3-methyl-6-(trans-4-pentyl cyclohexyl)tetrahydro-2-pyranone (Compound No. 6). The resulting compound was in the form of colorless crystals, and the yield based on the compound (36) was 37%.

Workup

  1. additionwas added dropwise
  2. customobtained in the first step
  3. customreacted at room temperature for 5 hours
  4. extractionextracted with 100 mL of dichloromethane
  5. washThe resulting organic layer was washed with water (150 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by column chromatography (developing solvent: heptane/ethyl acetate=9/1, column packing: silica gel)
  9. customrecrystallized from heptane

Sources & evidence

ORD record
ord-241566488c394a0db4184347eca4805d
Source dataset
uspto-grants-2011_01
Patent number
US07875327B2

Reaction notes

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