Sodium hydride → 2-Methyl-4-(6-carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole

HRID 972238노트

반응식

HRID 972238 반응식
[H-].[Na+].COP([CH2:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=O)OC.[CH3:17][C:18]1[S:19][C:20]([CH:33]=O)=[C:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[N:22]=1.C(CCCCCCC1N=CSC=1/C=C/C(=O)CCCCC)(OC)=O>COCCOC.O>[CH3:17][C:18]1[S:19][C:20](/[CH:33]=[CH:9]/[C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[N:22]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 214064152-Methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carbaldehydeHCID 214064184-(6-Carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole

생성물 1

HCID 214064192-Methyl-4-(6-carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매3회

실험 절차

To a suspension of 0.45 g of sodium hydride in 5 ml of anhydrous 1,2-dimethoxy-ethane a solution of 4.12 g of 2-oxoheptylphosphonic acid dimethyl ester in 20 ml of 1,2-dimethoxy-ethane was added under stirring at room temperature. The reaction mixture was stirred for an hour, then a solution of 1 g of 2-methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carbaldehyde (XIII, R1 = CH3) prepared according to point (e) of Example 2, in 10 ml of 1,2-dimethoxy-ethane was added dropwise, and stirring was continued for 5 hours. After adding dropwise 30 ml of water under ice-cooling to the reaction mixture, it was extracted with 3 × 20 ml of diethyl ether. The extract was dried on over sodium sulphate and evaporated in vacuo. The evaporation residue was purified by preparative thin layer chromatography, using a silica gel layer as adsorbent and a mixture of 40 % ethyl acetate and 60 % n-heptane as running solvent. The yield was 0.81 g of 2-methyl-4-(6-carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole (Ia, R1 = CH3) of chromatographic purity.

후처리

  1. additionwas added
  2. stirringThe reaction mixture was stirred for an hour
  3. additionwas added dropwise
  4. stirringstirring
  5. temperaturecooling to the reaction mixture, it
  6. extractionwas extracted with 3 × 20 ml of diethyl ether
  7. dry with materialThe extract was dried on over sodium sulphate
  8. customevaporated in vacuo
  9. customThe evaporation residue was purified by preparative thin layer chromatography
  10. additiona mixture of 40 % ethyl acetate and 60 % n-heptane

출처 및 근거

ORD 기록
ord-d83d930e1bb240348407ec1dac44fbec
출처 데이터셋
uspto-grants-1977_10
특허 번호
US04052407

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