Phenacyl bromide → Phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoate

HRID 728749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728749
[OH:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]([OH:6])=[O:5].[CH2:38](Br)[C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40].C(N(CC)CC)C>O1CCCC1>[OH:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]([O:6][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40])=[O:5]

Komponenten

5

Edukt 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 539401263-Hydroxy-2-n-tetradecyl-11-icosenoic acid

Produkt 1

HCID 53739963Phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoateAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Hydroxy-2-n-tetradecyl-11-icosenoic acid (II)(3.68 g, 7.04 millimole) was dissolved in dry tetrahydrofuran (100 ml), and phenacyl bromide (2.10 g, 10.56 millimole) and triethyl amine (1.47 ml, 10.56 millimole) were successively added thereto with ice cooling. The reaction mixture was allowed to warm to room temperature, and to react for 13.5 hours. The insoluble matter in the reaction mixture was filtered off with suction and the solvent was distilled off from the filtrate. The residue was dissolved in methylene chloride and the obtained solution was successively washed with water and saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The inorganic salt was filtered off and the solvent was distilled off from the filtrate. The obtained residue was purified over a silicagel column (benzene -→ benzene:ethyl acetate=8:2) to give phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoate (IV)(998.6 mg, yield 22.1%) in the form of white viscous solid. IR(νmaxKBr, cm-1); 3340, 2900, 2850, 1740, 1705

Aufarbeitung

  1. customto react for 13.5 hours
  2. filtrationThe insoluble matter in the reaction mixture was filtered off with suction
  3. distillationthe solvent was distilled off from the filtrate
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washthe obtained solution was successively washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe inorganic salt was filtered off
  8. distillationthe solvent was distilled off from the filtrate
  9. customThe obtained residue was purified over a silicagel column (benzene -→ benzene:ethyl acetate=8:2)

Quellen und Nachweise

ORD-Eintrag
ord-2df9f322f0c24fca9dd6ee783b2e70b2
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05049664

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