Tributylphosphine → HCID 21867689, 화합물

HRID 411142

반응식

HRID 411142 반응식
[OH:1][CH:2]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[CH2:3][CH:4]=[CH2:5].[CH3:14][O:15][C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[O:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=1)[CH2:3][CH:4]=[CH2:5]

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 162513,4-DimethoxyphenolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 110193454-(1-Hydroxy-3-butenyl)benzonitrile

생성물 1

HCID 21867689HCID 21867689, 화합물수율 68.6%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

A cooled (0° C.) mixture of 4-(1-hydroxy-3-butenyl)benzonitrile (14.6 g, 84.3 mmol) and 3,4-dimethoxyphenol (19.5 g, 125.4 mmol) in toluene (500 mL) was treated with tributylphosphine (32.14 mL of 97% purity, 25.6 g, 126.4 mmol), followed by 1,1′-(azodicarbonyl)dipiperidine (31.8 g, 126.4 mmol). After addition was complete, the reaction mixture thickened and the temperature rose to 15° C. Additional toluene was added (500 mL), and the mixture stirred at rt overnight. The precipitate of tributylphosphine oxide was then removed by filtration and the filtrate concentrated in vacuo to give 65.8 g of crude product. This was purified by chromatography on silica gel, eluting with toluene:methanol (98:2), to yield 17.9 g of the sub-title compound.

후처리

  1. temperatureA cooled
  2. additionAfter addition
  3. customrose to 15° C
  4. customThe precipitate of tributylphosphine oxide was then removed by filtration
  5. concentrationthe filtrate concentrated in vacuo
  6. customto give 65.8 g of crude product
  7. customThis was purified by chromatography on silica gel
  8. washeluting with toluene:methanol (98:2)

출처 및 근거

ORD 기록
ord-88a33979ca2345679982399a6e5a2de6
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559143B1

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