Triphenylphosphine → HCID 22650026、化合物

HRID 393301ノート

反応式

HRID 393301 の反応式
Br[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>C(NC(C)C)(C)C.CCCCCC.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:37][Si:38]([CH3:40])([CH3:39])[C:41]#[C:42][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH:3]=1

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 10107850HCID 10107850、化合物

生成物 1

HCID 22650026HCID 22650026、化合物収率 50%

試薬・触媒・溶媒 3

HCID 165397Cupric acetate monohydrate触媒HCID 7912Diisopropylamine溶媒HCID 8058Hexane溶媒

実験手順

To a stirred mixture of 4 (5.66 g, 20 mmol), dichlorobis(triphenylphosphine) palladium(II) (0.7 g, 1 mmol), copper(II) acetate hydrate (0.18 g, 1 mmol) and triphenyl-phosphine (0.52 g, 2 mmol) in 40 mL of diisopropyl amine was added trimethylsilyl acetylene (2.16 g, 22 mmol) and heated to reflux. On refluxing for an hour the mixture turns dark and solidifies. The reaction mixture was diluted with 50 mL of hexane and filtered. The filtrate was concentrated under reduced pressure and the residue was chromatographed over silica gel with hexane/methylene chloride (9:1 by volume) as eluant to yield 2.88 g (50 percent) of trimethyl[2-(5-methylene-5H-dibenzo[a,d]cyclohepten-10-yl)ethynyl)silane, 5, as a yellow oil.

後処理

  1. temperatureheated to reflux
  2. temperatureOn refluxing for an hour the mixture
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed over silica gel with hexane/methylene chloride (9:1 by volume) as eluant

出典と根拠

ORDレコード
ord-1938dc19cfc54d7684f8650cbf298e53
出典データセット
uspto-grants-2004_10
特許番号
US06806327B2

反応ノート

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