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

HRID 728749노트

반응식

HRID 728749 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 53739963Phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoate수율 22.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-2df9f322f0c24fca9dd6ee783b2e70b2
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049664

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