Methyl iodide → 4-[3-(1,4,4-Trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl ester

HRID 899290Notes

Reaction equation

HRID 899290 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH:12]([C:18]2[CH:27]=[C:26]3[C:21]([C:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][NH:25]3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.[CH3:31][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>C1COCC1>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH:11][CH:12]([C:18]2[CH:27]=[C:26]3[C:21]([C:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][N:25]3[CH3:31])=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 692164454-[3-(4,4-Dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl ester

Product 1

HCID 692157304-[3-(1,4,4-Trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[3-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl ester (0.36 g, 0.88 mmole) in 10 mL of THF was cooled to −78° C. and was treated with 1.1 mL of a 1M lithium bis(trimethylsilyl)amide solution in hexanes. After 30 minutes at −78° C., 0.06 mL of methyl iodide was added. The mixture was stirred at room temperature for 7 hours, quenched by the addition of 10 mL of saturated aqueous ammonium chloride solution and extracted with two 10 mL portions of ethyl acetate. 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 0.23 g of 4-[3-(1,4,4-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl ester as a pale yellow oil.

Workup

  1. customquenched by the addition of 10 mL of saturated aqueous ammonium chloride solution
  2. extractionextracted with two 10 mL portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ab3fd3b3cdbf45e3a4cc9773d0e6016d
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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