Triethylamine → HCID 131718070, compound

HRID 2254652Notes

Reaction equation

HRID 2254652 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([CH2:9][CH2:10][CH2:11][C@H:12]([CH2:14][CH2:15][CH2:16]/[C:17](=[CH:19]/[CH2:20][OH:21])/[CH3:18])[CH3:13])[CH3:8])[CH3:3].C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1>C(Cl)Cl>[C:29]([O:21][CH2:20]/[CH:19]=[C:17](/[CH2:16][CH2:15][CH2:14][C@@H:12]([CH2:11][CH2:10][CH2:9][C@@H:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:8])[CH3:13])\[CH3:18])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 5280435Phytol

Product 1

HCID 131718070HCID 131718070, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture consisting of 10 0 g of phytol, 9.0 g of triethylamine and 50 ml of methylene chloride was added 7.2 g of nicotinic chloride at 30°-40° C. The resulting mixture was stirred for 2 hours at the same temperature. After the completion of the reaction, the reaction mixture was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant; n-hexane:ethyl acetate=9:1) to obtain 12.1 g (yield: 90%) of oily phytyl nicotinate.

Workup

  1. customAfter the completion of the reaction
  2. washthe reaction mixture was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue obtained
  6. customwas purified by a column chromatography (eluant; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f3c2fbd12c684c84ab579c8b49417e2c
Source dataset
uspto-grants-1993_08
Patent number
US05236950

Reaction notes

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