Methyl iodide → 5,7-Bis(methoxymethoxy)-2-methylthiochromone

HRID 441053

반응식

HRID 441053 반응식
[H-].[K+].[OH:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:7]=[C:6]([O:14][CH2:15][O:16][CH3:17])[C:5]=1[C:18](=O)[CH3:19].C1O[CH2:37][CH2:36]OCCOCCOCCOCCOC1.C(=S)=[S:40].CI>C1COCC1.O>[CH3:17][O:16][CH2:15][O:14][C:6]1[CH:7]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:9]=[C:4]2[C:5]=1[C:18](=[S:40])[CH:19]=[C:36]([CH3:37])[O:3]2

참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 2855718-Crown-6HCID 82127Potassium hydrideHCID 108796971-[2-Hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone

생성물 1

HCID 570855075,7-Bis(methoxymethoxy)-2-methylthiochromone수율 91.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Under cooling on ice, potassium hydride (0.5 ml of 35% mineral oil) was suspended in 2 ml THF. 2 ml of 126 mg of 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone (0.492 mmol) and 130 mg of 18-crown-6 (0.492 mmol) in THF was added dropwise to the above suspension, and the mixture was stirred for 1 hour. After addition of 0.89 ml of carbon disulfide (14.76 mmol), the solution was stirred for 20 hours at room temperature. Then, 0.5 ml of methyl iodide was added thereto, and the solution was stirred for 30 min. After water was slowly added thereto, the reaction solution was extracted twice with ether, and the organic layer was washed with saturated NaCl water and then dried over sodium sulfate anhydride. The solvent was distilled off and the resulting crude product was washed with hexane, to give 133.5 mg of 5,7-bis(methoxymethoxy)-2-methylthiochromone (87% yield).

후처리

  1. stirringthe solution was stirred for 20 hours at room temperature
  2. stirringthe solution was stirred for 30 min
  3. extractionthe reaction solution was extracted twice with ether
  4. washthe organic layer was washed with saturated NaCl water
  5. dry with materialdried over sodium sulfate anhydride
  6. distillationThe solvent was distilled off
  7. washthe resulting crude product was washed with hexane

출처 및 근거

ORD 기록
ord-81be17509c404bde932adfb2225d6ac0
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521216

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