Tetramethyltin → 1-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)ethanone

HRID 2294590노트

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HRID 2294590 반응식
[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[C:14]([OH:16])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)(Cl)=O.[CH3:26]N(C)P(N(C)C)(N(C)C)=O.C[Sn](C)(C)C>C1(C)C=CC=CC=1.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Pd+2].O>[C:1]12([C:11]3[CH:12]=[C:13]([C:14](=[O:16])[CH3:26])[CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

참가 물질

8

반응물 4

HCID 11661TetramethyltinHCID 12679HexamethylphosphoramideHCID 24386Thionyl ChlorideHCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid

생성물 1

HCID 106368221-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)ethanone

시약·촉매·용매 3

HCID 6097231Methanidylbenzene;palladium(2+);triphenylphosphane;chloride촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

15.75 g (0.055 mol) of 3-(1-adamantyl)-4-methoxybenzoic acid, dissolved in 150 ml of toluene, are treated with 7.3 ml of thionyl chloride and heated to 100° C., for 3 h 30 min. The reaction medium is evaporated to dryness and 30 ml of hexamethylphosphoramide, 8 ml (0.0575 mol) of tetramethyltin and 22 mg of benzylbis(triphenylphosphine)palladium(II) chloride are then added under nitrogen to this evaporation residue. The reaction medium is heated to 65° C., for 30 min and is then left stirring at room temperature overnight. The reaction medium is poured into water and the mixture is extracted with ether. After chromatography on silica, 10.47 g (71%) of the expected derivative, melting point 138°-140° C., are isolated in the dichloromethane/hexane (60:40) eluent.

후처리

  1. additionare then added under nitrogen to this evaporation residue
  2. temperatureThe reaction medium is heated to 65° C., for 30 min
  3. waitis then left
  4. extractionthe mixture is extracted with ether
  5. customAfter chromatography on silica, 10.47 g (71%) of the expected derivative, melting point 138°-140° C., are isolated in the dichloromethane/hexane (60:40) eluent

출처 및 근거

ORD 기록
ord-4b8244a560184841a8eb3dd1f14fe431
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05688817

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