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

HRID 1611730
ノート
印刷プレビュー

反応式

HRID 1611730 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 542087336-Benzylidene-2,4-di-tert-butyl-cyclohexa-2,4-dienone2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-7fb6dfad001e4eb289da315bb5973d59
出典データセット
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06989446B2

反応ノート

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