Allyl bromide → HCID 178459151, 화합물

HRID 1029343노트

반응식

HRID 1029343 반응식
[H-].[Na+].[CH3:3][O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1.[CH2:20](Br)[CH:21]=[CH2:22]>O1CCCC1>[CH2:20]([O:19][CH2:18][C@H:15]1[CH2:14][CH2:13][C@H:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([CH2:5][O:4][CH3:3])[CH2:7][CH2:8]2)[CH2:17][CH2:16]1)[CH:21]=[CH2:22]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178495625HCID 178495625, 화합물

생성물 1

HCID 178459151HCID 178459151, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
70 °C

실험 절차

150 mg of sodium hydride (as a 50 percent suspension in oil) is suspended in 10 ml of absolute tetrahydrofuran and then treated dropwise at room temperature within 3 minutes with a solution of 0.5 g of [trans-4-[trans-4-(methoxymethyl)cyclohexyl]cyclohexyl]methanol in 8 ml of absolute tetrahydrofuran. The mixture is stirred for a further 5 minutes, then treated with 0.755 g of allyl bromide and stirred under reflux (bath temperature 70° C.) for 16 hours. Thereafter, the reaction mixture is partitioned in diethyl ether/water and extracted three times with diethyl ether. The organic phases are washed twice with water, dried over magnesium sulphate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gives [trans-4-[trans-4-(methoxymethyl)cyclohexyl]cyclohexyl]methyl allyl ether.

후처리

  1. stirringstirred
  2. customThereafter, the reaction mixture is partitioned in diethyl ether/water
  3. extractionextracted three times with diethyl ether
  4. washThe organic phases are washed twice with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

출처 및 근거

ORD 기록
ord-eecfe7d4e7054e1389329de96d52bd07
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102578

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