2-Methyl-2-butene → HCID 58026119, compound

HRID 2387319Notes

Reaction equation

HRID 2387319 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([CH3:22])([CH3:21])[CH2:11][C@:12]([OH:20])([C:16]([F:19])([F:18])[F:17])[CH2:13][C:14]#[CH:15])=[C:6]([CH:9]=1)[CH:7]=[O:8].CC(=CC)C.Cl([O-])=[O:29].[Na+].P([O-])([O-])(O)=O.[Na+].[Na+]>C(O)(C)(C)C.C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([CH3:22])([CH3:21])[CH2:11][C@:12]([OH:20])([C:16]([F:18])([F:19])[F:17])[CH2:13][C:14]#[CH:15])=[C:6]([CH:9]=1)[C:7]([OH:29])=[O:8]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 24203Sodium Phosphate, DibasicHCID 23668197Sodium ChloriteHCID 58026141HCID 58026141, compound

Product 1

HCID 58026119HCID 58026119, compoundYield 103%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15 g (0.031 mol) of 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzaldehyde in 240 mL of tert-BuOH was added a solution of the 62 mL (0.124 mol) of 2-methyl-2-butene in THF (2 M). To this solution was added a solution of the 17.5 g of sodium chlorite (0.150 mol) and 42.8 g of sodium hydrogen phosphate (0.138 mol) in water. The reaction mixture was stirred overnight. The volatiles were removed in vacuo. The aqueous mixture was then acidified to pH=1 with 1 M HCl, extracted with 1200 mL of ethyl acetate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was chromatographed on silica gel using 10-100% ethyl acetate/hexanes to afford 10.6 g (103%) of 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzoic acid.

Workup

  1. customThe volatiles were removed in vacuo
  2. extractionextracted with 1200 mL of ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was chromatographed on silica gel using 10-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1af0914e55464e7692fa56dbcfc4834d
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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