2-Phenyl-1,3-dithiane → HCID 86634585, 화합물

HRID 73472

반응식

HRID 73472 반응식
[C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:18]([Ge:20](Cl)([Cl:23])[CH2:21][CH3:22])[CH3:19]>O1CCCC1.CCCCCC>[Cl:23][Ge:20]([CH2:21][CH3:22])([CH2:18][CH3:19])[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:8][CH2:9][CH2:10][CH2:11][S:12]1

참가 물질

6

반응물 3

HCID 215472-Phenyl-1,3-dithianeHCID 83334DichlorodiethylgermaneHCID 178418339Butyllithium

생성물 1

HCID 86634585HCID 86634585, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-10 °C

실험 절차

19.63 g (0.10 mol) 2-phenyl-1,3-dithian was dissolved under argon in 200 ml anhydrous tetrahydrofuran (THF) in a dry 500-ml three-necked flask with 50 ml dropping funnel, internal thermometer, magnetic stirrer and septum. The solution was cooled to −10° C. 44 ml of a 2.5 molar solution of n-butyllithium (0.11 mol) in n-hexane was added dropwise at −5° C. over a period of 50 min. After the addition was complete, the green solution was stirred for 2 h at 0° C. It was then added dropwise within 45 min to a solution, cooled to −72° C., of 20.16 g (0.10 mol) diethylgermanium dichloride in 500 ml anhydrous THF, wherein the temperature did not exceed −65° C. The reaction mixture was stirred for a further 16 h in a thawing cold bath, then concentrated on the rotary evaporator. 100 ml dry n-hexane was added to the residue followed by stirring for 1 h at room temperature. The suspension was filtered and the filtrate was concentrated on the rotary evaporator and dried under fine vacuum. The oily, yellow crude product was purified by means of high-vacuum distillation (b.p.: 135-150° C./4×10−5 mbar). 27.23 g (75% of the theoretical value) chlorodiethyl(2-phenyl-1,3-dithian-2-yl)germanium was obtained as a yellow oil.

후처리

  1. additionAfter the addition
  2. additionIt was then added dropwise within 45 min to a solution
  3. customdid not exceed −65° C
  4. stirringThe reaction mixture was stirred for a further 16 h in a thawing cold bath
  5. concentrationconcentrated on the rotary evaporator
  6. addition100 ml dry n-hexane was added to the residue
  7. stirringby stirring for 1 h at room temperature
  8. filtrationThe suspension was filtered
  9. concentrationthe filtrate was concentrated on the rotary evaporator
  10. customdried under fine vacuum
  11. distillationThe oily, yellow crude product was purified by means of high-vacuum distillation (b.p.: 135-150° C./4×10−5 mbar)

출처 및 근거

ORD 기록
ord-3df9e9425e1042579735a9497a7af661
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829067B2

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