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Nitrogen → 4,4'-Tolan-dicarboxylic acid di-tert.-butyl ester

HRID 974209
ノート
印刷プレビュー

反応式

HRID 974209 の反応式
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N#N.[C:36]([O:40][C:41](=[O:50])[C:42]1[CH:47]=[CH:46][C:45]([C:48]#[CH:49])=[CH:44][CH:43]=1)([CH3:39])([CH3:38])[CH3:37]>C(#N)C.[Cu]I.CCN(CC)CC>[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:49]#[C:48][C:45]2[CH:46]=[CH:47][C:42]([C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:50])=[CH:43][CH:44]=2)=[CH:9][CH:8]=1)=[O:14])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 947NitrogenHCID 11776TriphenylphosphineHCID 11334366Tert-butyl 4-bromobenzoateHCID 13965008Tert-butyl 4-ethynylbenzoate

生成物 1

HCID 148475264,4'-Tolan-dicarboxylic acid di-tert.-butyl ester

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 6342Acetonitrile溶媒2 回
HCID 8471Triethylamine溶媒

実験手順

4-Bromo-benzoic acid tert.-butyl ester, 5.1 g of triphenylphosphine and 375 ml of NEt3 are introduced into 1 l of absolute acetonitrile under nitrogen and N2 is passed through the solution for 20 minutes. 10.5 g of (Pφ3)2PdCl2 and 1.5 g of copper(I)iodide are then added and 166.5 g of 4-ethinyl-benzoic acid tert.-butyl ester dissolved in 1 l of absolute acetonitrile are slowly added dropwise under reflux and the reaction mixture is stirred overnight. The resulting reaction mixture is then suction filtered after cooling, stirred up in water, again suction filtered, dissolved in CH2Cl2 and filtered after the addition of a small quantity of Tonsil, and the solvent is then evaporated off under vacuum. 225 g of 4,4'-Tolan-dicarboxylic acid-di-tert.-butyl ester are obtained.

後処理

  1. additionare slowly added dropwise
  2. temperatureunder reflux
  3. customThe resulting reaction mixture
  4. filtrationsuction filtered
  5. temperatureafter cooling
  6. stirringstirred up in water
  7. filtrationagain suction filtered
  8. dissolutiondissolved in CH2Cl2
  9. filtrationfiltered
  10. additionafter the addition of a small quantity of Tonsil
  11. customthe solvent is then evaporated off under vacuum

出典と根拠

ORDレコード
ord-8b63aad949984d1eb9e3fd6260dad1c3
出典データセット
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05068300

反応ノート

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