2,4,6-Trimethylpyridine → Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate

HRID 892637

반응식

HRID 892637 반응식
[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH:22]([CH3:24])[CH3:23])=[CH:6][CH:7]=[C:8]([CH3:21])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:20])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:19])[CH2:17]O)[CH3:2].CC1C=C(C)N=C(C)C=1.[Cl-].[Li+].CS([Cl:41])(=O)=O>C(OCC)C.O.CN(C)C=O>[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH:22]([CH3:24])[CH3:23])=[CH:6][CH:7]=[C:8]([CH3:21])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:20])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:19])[CH2:17][Cl:41])[CH3:2]

참가 물질

8

반응물 4

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 54363154Ethyl 14-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate

생성물 1

HCID 54546229Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate수율 88%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of the hydroxyester compound which is 14-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoic acid ethyl ester (71.0 mg, 0.20 mmol), S-collidine (26.7 mg, 0.22 mmol), lithium chloride (8.5 mg, 0.20 mmol) and dimethylformamide (1 ml) is added methanesulfonyl chloride (25.2 mg, 0.22 mmol) under nitrogen atmosphere while stirring on an ice-bath. The stirring is continued at the same temperature for 5 hours. After confirming disappearance of the starting compound, to the reaction mixture are added water and ethyl ether and the organic layer is separated. The organic layer is washed with water, dried (MgSO4) and concentrated. The resulting residue is chromatographed (n-hexane/ethyl acetate =10:1) on silica gel column to give the desired 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoic acid ethyl ester (64.6 mg, 86%) from the desired fraction.

후처리

  1. customthe organic layer is separated
  2. washThe organic layer is washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting residue is chromatographed (n-hexane/ethyl acetate =10:1) on silica gel column

출처 및 근거

ORD 기록
ord-2ae31746d8a5474cb6a1675c71217cd2
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05118827

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