7-(3,3-dibromo-1-pentyl-allyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester → 4,4-dimethyl-7-(1-pentyl-prop-2-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 2415213Notes

Reaction equation

HRID 2415213 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:19]=[C:20](Br)Br)[CH:16]=2)[C:11]([CH3:29])([CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:19]#[CH:20])[CH:16]=2)[C:11]([CH3:28])([CH3:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 865890277-(3,3-dibromo-1-pentyl-allyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 865890284,4-dimethyl-7-(1-pentyl-prop-2-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 7-(3,3-dibromo-1-pentyl-allyl)-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.08 g, 0.15 mmole) in 2 mL of THF at −78° C. was treated with 0.13 mL of 2.5M butyllithium. The reaction mixture was stirred at −78° C. for 1 hour, then at room temperature for 2 hours, quenched by the successive addition of 5 mL water and 5 mL of saturated aqueous ammonium chloride solution and extracted with three 25 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes) to yield 0.049 g of 4,4-dimethyl-7-(1-pentyl-prop-2-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as a colourless oil.

Workup

  1. waitat room temperature for 2 hours
  2. customquenched by the successive addition of 5 mL water and 5 mL of saturated aqueous ammonium chloride solution
  3. extractionextracted with three 25 mL portions of ether
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b231714612134ad09d1e296740ea8480
Source dataset
uspto-grants-2004_11
Patent number
US06818652B2

Reaction notes

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