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Diethyl Ether → HCID 178418606, 화합물

HRID 5304
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HRID 5304 반응식
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3C=C[C:34]([C:37]#N)=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.[C:39](=[O:42])([O-])[O-].[Na+].[Na+].[CH2:45](OCC)C>O1CCCC1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([C:25]2([C:39](=[O:42])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:30]=[CH:29][C:28]([C:31]3[CH:45]=[CH:37][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH2:26]2)[CH2:23][CH2:24]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 178418638HCID 178418638, 화합물HCID 178418655HCID 178418655, 화합물

생성물 1

HCID 178418606HCID 178418606, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of nonylmagnesium bromide (8.3 mmol) in 30 ml of diethyl ether was treated at 0° C. with a solution of 1.5 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 15 ml of tetrahydrofuran. The reaction mixture was heated at slight reflux overnight and then treated with dilute sodium carbonate solution. The organic phase was separated and the aqueous phase was back-extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed once with dilute sodium carbonate solution and twice with water and then dried over magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). The trans-4-(4-decanoyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether (1.8 g) obtained was used in the next step without further purification.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat slight reflux overnight
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was back-extracted three times with 50 ml of diethyl ether each time
  5. washThe combined organic phases were washed once with dilute sodium carbonate solution and twice with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)

출처 및 근거

ORD 기록
ord-5ec990aeb1174b278ed38ed7122071bb
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05244597

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