Triethylamine → ethyl (S)-3-methoxymethoxytetradecanoate

HRID 1821146Notes

Reaction equation

HRID 1821146 reaction equation
[OH:1][C@@H:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].ClC[C:22]([O:24][CH2:25]OC)=C.C(N(CC)CC)C>C1COCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:22][O:24][CH2:25][O:1][C@@H:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 106782943-Chloro-2-(methoxymethoxy)prop-1-eneHCID 56845842Ethyl (3S)-3-hydroxytetradecanoate

Product 1

HCID 86613490ethyl (S)-3-methoxymethoxytetradecanoateYield 95.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (S)-3-hydroxytetradecanoate (2.00 g, 7.3 mmol) and 2-(chloromethyl)-3,5-dioxahexa-1-ene (manufactured by Tokyo Kasei Co., Ltd., 1.20 g, 8.8 mmol) were dissolved in THF (10 mL), p-toluenesulfonic acid (p-TsOH, 10 mg) was added, and the mixture was stirred at room temperature for 15 hr. Triethylamine (1 mL) was poured into the reaction mixture and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate (0.5 g) and filtered. The solvent was evaporated to give the corresponding ethyl (S)-3-methoxymethoxytetradecanoate (2.20 g, yield 95%).

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate solution (10 mL) and saturated brine (10 mL)
  2. dry with materialdried over anhydrous magnesium sulfate (0.5 g)
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4a9632f4cba44fbca1e3ef6df96fac0b
Source dataset
uspto-grants-2009_10
Patent number
US07605286B2

Reaction notes

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