Potassium Hydroxide → HCID 11208062, compound

HRID 1760837Notes

Reaction equation

HRID 1760837 reaction equation
FC(F)(F)C([N:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=2[CH:7]=1)=O.[OH-].[K+]>C(O)C.O>[CH2:20]([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:18])([CH3:19])[C:8]=2[CH:7]=1)[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 113945882,2,2-trifluoro-N-pentyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide

Product 1

HCID 11208062HCID 11208062, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2,2,2-trifluoro-N-pentyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (31) (13.6 g, 37.5 mmole) in 140 mL ethanol was treated with a solution of potassium hydroxide (10.52 g) in 25 mL water. The mixture was stirred at room temperature for two hours, diluted with 100 mL water and then extracted with two 250 mL portions of ethyl acetate. The combined organic extracts were washed with six 200 mL portions of cold water or until the pH was neutral. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes) to yield 9.86 g of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (33) as a golden oil.

Workup

  1. extractionextracted with two 250 mL portions of ethyl acetate
  2. washThe combined organic extracts were washed with six 200 mL portions of cold water or until the pH
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bf55d13130c34db9b8bbef4034cbacf0
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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