Trifluoroacetic acid → 5,7-Bis(1,1-dimethylethyl)-3-phenyl-(3H)-benzofuran-2-one

HRID 2228820

반응식

HRID 2228820 반응식
[CH:1](=[C:8]1[C:13](=[O:14])[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)[C:25](O)=[O:26]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]([C:10]1[CH:11]=[C:12]([C:15]([CH3:16])([CH3:18])[CH3:17])[C:13]2[O:14][C:25](=[O:26])[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]=2[CH:9]=1)([CH3:22])([CH3:21])[CH3:20]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 54208733HCID 54208733, 화합물2회

생성물 1

HCID 64553565,7-Bis(1,1-dimethylethyl)-3-phenyl-(3H)-benzofuran-2-one수율 90%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

A solution of 589 mg (2.0 mmol) of a mixture of 6-benzylidene-2,4-di-tert-butyl-cyclohexa-2,4-dienone (compound (302), Table 3) and the corresponding dimer (compound (402), Table 4), prepared according to Example 2b, in 7 ml of toluene is degassed using argon and then 58 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(0) and 23 mg (0.20 mmol) of trifluoroacetic acid are added. The autoclave is flushed with carbon monoxide and sealed, and a carbon monoxide pressure of 5 bar is then applied. The reaction mixture is maintained at 80° C. for 20 hours. After cooling to room temperature, the reaction mixture is poured into water and extracted three times using ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated using a vacuum rotary evaporator. Crystallisation of the residue from isopropanol yields 580 mg (90%) of 5,7-di-tert-butyl-3-phenyl-3H-benzofuran-2-one (compound (102), Table 1), m.p. 116-119° C. Analysis, calculated: C 81.95; H 8.13%. Analysis, found: C 81.93; H 8.13%.

후처리

  1. customis degassed
  2. customThe autoclave is flushed with carbon monoxide
  3. customsealed
  4. temperatureAfter cooling to room temperature
  5. additionthe reaction mixture is poured into water
  6. extractionextracted three times
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customa vacuum rotary evaporator
  10. customCrystallisation of the residue from isopropanol

출처 및 근거

ORD 기록
ord-b138b9276b3943aba5d476e133a66085
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417358B1

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