Trifluoroacetic acid → (4R)-4,8-Dimethylnonanoic acid

HRID 1829845Notes

Reaction equation

HRID 1829845 reaction equation
C([O:5][C:6](=[O:17])[CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:16][C@H:9]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH2:7][C:6]([OH:17])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71406104tert-butyl (4R)-4,8-dimethylnonanoate

Product 1

HCID 71351570(4R)-4,8-Dimethylnonanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4R)-4,8-dimethyl nonanoic acid t-butyl ester in 25 mL CH2Cl2 at 0° C. was treated with TFA (6 mL). The mixture was allowed to reach ambient temperature and stir overnight. The solvent was removed by rotary evaporation, and the mixture was purified by silica gel chromatography (95/5 hexane/EtOAc) to give 0.962 g (4R)-4,8-dimethyl nonanoic acid. m/z 185 (M−).

Workup

  1. customto reach ambient temperature
  2. customThe solvent was removed by rotary evaporation
  3. customthe mixture was purified by silica gel chromatography (95/5 hexane/EtOAc)

Sources & evidence

ORD record
ord-fc3f4df650e14fc6ac4203787404fd1e
Source dataset
uspto-grants-2006_06
Patent number
US07064147B2

Reaction notes

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