Water → HCID 86634584, 화합물

HRID 73471

반응식

HRID 73471 반응식
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:32]=[CH:31][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[S:30][CH2:29][CH2:28][CH2:27][S:26]3)=[CH:21][CH:20]=2)=[CH:9][CH:8]=1.C([Li])CCC.[CH3:38][Ge:39](Cl)([CH3:41])[CH3:40].O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:38][Ge:39]([CH3:41])([CH3:40])[C:2]1([C:7]2[CH:32]=[CH:31][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4([Ge:39]([CH3:41])([CH3:40])[CH3:38])[S:26][CH2:27][CH2:28][CH2:29][S:30]4)=[CH:21][CH:20]=3)=[CH:9][CH:8]=2)[S:3][CH2:4][CH2:5][CH2:6][S:1]1

참가 물질

8

반응물 4

HCID 962WaterHCID 73723ChlorotrimethylgermaneHCID 86634583HCID 86634583, 화합물HCID 178418339Butyllithium

생성물 1

HCID 86634584HCID 86634584, 화합물

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-10 °C

실험 절차

A suspension of 8.11 g (16.0 mmol) 1,6-bis[4-(1,3-dithian-2-yl)phenoxy]hexane in 50 ml anhydrous tetrahydrofuran (THF) was prepared under argon in a dry 250-ml three-necked flask with 50 ml dropping funnel, internal thermometer, magnetic stirrer and septum. The suspension was cooled to −10° C. and 14.1 ml of a 2.5 molar solution of n-butyl lithium (35.2 mmol) in hexane added dropwise over a period of 10 min such that the internal temperature did not exceed 0° C. The brown solution was then stirred for 3 h at −10° C. and a solution of 4.90 g (32.0 mmol) trimethylgermanium chloride in 20 ml anhydrous THF added dropwise to it at −5° C. within 5 min. The reaction mixture was stirred for a further 24 h at room temperature. 50 ml water and 150 ml ethyl acetate were then added and the resultant phases separated. The organic phase was washed twice with 50 ml each time and the combined aqueous phases were re-extracted with 50 ml ethyl acetate. Finally, the combined organic phases were washed with 80 ml saturated aqueous NaCl solution and dried over anhydrous sodium sulphate. After separating off the desiccant, the reaction mixture was concentrated on the rotary evaporator and the product dried to constant weight under fine vacuum. 10.9 g (92% of the theoretical value) 1,6-bis{4-[2-(trimethylgermyl)-1,3-dithian-2-yl]phenoxy}hexane was obtained as a pale-yellowish solid (m.p.: 147-153° C.).

후처리

  1. customwas prepared under argon in a dry 250-ml three-necked flask with 50 ml
  2. customdid not exceed 0° C
  3. stirringThe reaction mixture was stirred for a further 24 h at room temperature
  4. customthe resultant phases separated
  5. washThe organic phase was washed twice with 50 ml each time
  6. extractionthe combined aqueous phases were re-extracted with 50 ml ethyl acetate
  7. washFinally, the combined organic phases were washed with 80 ml saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous sodium sulphate
  9. customAfter separating off the desiccant
  10. concentrationthe reaction mixture was concentrated on the rotary evaporator
  11. customthe product dried to constant weight under fine vacuum

출처 및 근거

ORD 기록
ord-b48936d8de9c49ff99c12048be15c5d3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829067B2

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