Triphenylphosphine → 1,2-Benzisoxazole

HRID 641939노트

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HRID 641939 반응식
O[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1/[CH:4]=[N:5]/[OH:6].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[O:6]1[C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[CH:4]=[N:5]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 135408751Salicylaldoxime

생성물 1

HCID 710731,2-Benzisoxazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
4 °C

실험 절차

Into a 1 L 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (E)-2-hydroxybenzaldehyde oxime (3 g, 21.90 mmol) in tetrahydrofuran (300 mL). To the mixture was added PPh3 (6.024 g, 22.99 mmol), while cooling to a temperature of 4° C. This was followed by the addition of a solution of DEAD (4 g, 22.99 mmol) in tetrahydrofuran (150 mL), while cooling to a temperature of 4° C. over a time period of 4 hours. The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at 4° C. in a bath of H2O/ice. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a column with a 1:100 ethyl acetate/petroleum ether solvent system. This resulted in 1.8 g (66%) of benzo[d]isoxazole as yellow oil.

후처리

  1. customInto a 1 L 3-necked round bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperaturewhile cooling to a temperature of 4° C. over a time period of 4 hours
  4. customto react
  5. concentrationThe mixture was concentrated by evaporation under vacuum
  6. customa rotary evaporator
  7. customThe residue was purified
  8. washby eluting through a column with a 1:100 ethyl acetate/petroleum ether solvent system
  9. customThis resulted in 1.8 g (66%) of benzo[d]isoxazole as yellow oil

출처 및 근거

ORD 기록
ord-40b9d44f48734ace86bf058ef69f8e93
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696229B2

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