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

HRID 2294590ノート

反応式

HRID 2294590 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6097231Methanidylbenzene;palladium(2+);triphenylphosphane;chloride触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4b8244a560184841a8eb3dd1f14fe431
出典データセット
uspto-grants-1997_11
特許番号
US05688817

反応ノート

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