HCID 11349373, compound → HCID 11484086, compound

HRID 382996Notes

Reaction equation

HRID 382996 reaction equation
C([O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:25])([CH3:24])[CH2:11][C:12]#[C:13][C:14]([C:20]([F:23])([F:22])[F:21])([OH:19])[C:15]([F:18])([F:17])[F:16])(C)(C)C.[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OC)(C)(C)C>[F:16][C:15]([F:17])([F:18])[C:14]([C:20]([F:21])([F:22])[F:23])([OH:19])/[CH:13]=[CH:12]\[CH2:11][C:10]([CH3:25])([CH3:24])[CH2:9][CH2:8][CH2:7][CH2:6][OH:5]

Participants

5

Reactant 2

HCID 11349373HCID 11349373, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11484086HCID 11484086, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 15413tert-Butyl methyl etherSolvent

Procedure

A suspension of 22.13 g of 10-tert-butoxy-1,1,1-trifluoro-6,6-dimethyl-2-trifluoromethyl-dec-3-yn-2-ol, 220 ml of tert-butylmethyl ether and 3.32 g of Lindlar catalyst was hydrogenated at 22° and 1 bar for 1.5 h after which time hydrogen up-take ceased. The suspension was filtered, the filtrate evaporated and the residue, containing pure (Z)-10-tert -butoxy-1,1,1-trifluoro-6,6-dimethiyl-2-trifluoromethyl-dec-3-en-2-ol, was dissolved in 44 ml of isopropanol. The solution was treated with 22.8 g of 50% aqueous H2SO4 and the mixture was heated to 90° for 2 h after which time g.l.c. indicated completion of the reaction. The mixture was evaporated, the residue partitioned between dichloromethane and saturated NaHCO3 solution and the aqueous layer was extracted several times with dichloromethane. The combined ortganic layers were dried over MgSO4 and evaporated to give 17.97 g of the pure title compound as a colorless oil.

Workup

  1. customwas hydrogenated at 22°
  2. filtrationThe suspension was filtered
  3. customthe filtrate evaporated
  4. additionthe residue, containing pure (Z)-10-tert -butoxy-1,1,1-trifluoro-6,6-dimethiyl-2-trifluoromethyl-dec-3-en-2-ol
  5. dissolutionwas dissolved in 44 ml of isopropanol
  6. additionThe solution was treated with 22.8 g of 50% aqueous H2SO4
  7. temperaturethe mixture was heated to 90° for 2 h after which time g.l.c
  8. customcompletion of the reaction
  9. customThe mixture was evaporated
  10. customthe residue partitioned between dichloromethane and saturated NaHCO3 solution
  11. extractionthe aqueous layer was extracted several times with dichloromethane
  12. dry with materialThe combined ortganic layers were dried over MgSO4
  13. customevaporated

Sources & evidence

ORD record
ord-e8d3f8f86bac42939bd740301c2824ac
Source dataset
uspto-grants-2001_10
Patent number
US06310262B1

Reaction notes

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