1-Iodopentane → 2,2,2-trifluoro-N-pentyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide

HRID 1760836Notes

Reaction equation

HRID 1760836 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=2[CH:7]=1)=[O:4].[OH-].[K+].I[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CS(C)=O.O>[F:1][C:2]([F:20])([F:21])[C:3]([N:5]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:16])([CH3:17])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=2[CH:7]=1)=[O:4]

Participants

6

Reactant 3

HCID 123351-IodopentaneHCID 14797Potassium HydroxideHCID 11472073HCID 11472073, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,2,2-trifluoro-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (29) (15.05 g, 40.7 mmole) in 105 mL dimethylsulfoxide (DMSO) was treated with potassium hydroxide (3.38 g) and then cooled to 0° C. Iodopentane (7.9 mL) in 15 mL DMSO was added dropwise to the reaction mixture and the temperature was allowed to rise to 23° C. The reaction mixture was stirred at room temperature for 24 hours, diluted with 200 mL of water and extracted with two 200 mL portions of ether. The combined organic extracts were washed with four 200 mL portions of cold water, dried over MgSO4, filtered and concentrated in vacuo to give a brown oil. The product was purified by flash chromatography (SiO2, 1:15 ethyl acetate/hexanes) to afford 14.36 g of 2,2,2-trifluoro-N-pentyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (31) as a pale yellow oil.

Workup

  1. customto rise to 23° C
  2. extractionextracted with two 200 mL portions of ether
  3. washThe combined organic extracts were washed with four 200 mL portions of cold water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil
  8. customThe product was purified by flash chromatography (SiO2, 1:15 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6c1045462787488db7b7c7823bd64e45
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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