Pyridoxal hydrochloride → 2-Methyl-3-hydroxy-4-formyl-5-(z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine

HRID 1268430

반응식

HRID 1268430 반응식
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:21][C:22]1[C:27]([OH:28])=[C:26]([CH:29]=[O:30])[C:25]([CH2:31][OH:32])=[CH:24][N:23]=1.Cl.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:21][C:22]1[C:27]([OH:28])=[C:26]([CH:29]=[O:30])[C:25]([CH2:31][O:32][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:24][N:23]=1

참가 물질

6

반응물 3

HCID 6171Pyridoxal hydrochlorideHCID 8471TriethylamineHCID 11770936gamma-Linolenoyl Chloride

생성물 1

HCID 867589562-Methyl-3-hydroxy-4-formyl-5-(z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of z,z,z-octadeca-6,9,12-trienoyl chloride (800 mg, 2.7 mmol) in methylene chloride (10 ml) was added slowly dropwise to a mixture of pyridoxal hydrochloride (500 mg, 2.45 mmol), triethylamine (1 ml, 7.2 mmol) and 4-(N,N-dimethylamino)pyridine (few mg, catalytic amount) in methylene chloride (20 ml) at 0° C. under nitrogen. On completion, as indicated by tlc, the mixture was concentrated and purified by flash chromatography (ethyl acetate/hexane), yielding 2-methyl-3-hydroxy-4-formyl-5-( z,z,z-octadeca-6,9,12-trienoyloxy)methyl pyridine as a colourless oil which subsequently solidified.

후처리

  1. concentrationthe mixture was concentrated
  2. custompurified by flash chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-96f801c1831e4ea8aeee2d7e0ed1cb38
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555700B1

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