Water → HCID 22117537、化合物

HRID 1275795ノート

反応式

HRID 1275795 の反応式
[C-:1]#[CH:2].[Li+].C(N)CN.Br[C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.O>CN(P(N(C)C)(N(C)C)=O)C.CCOCC>[C:1]([C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)#[CH:2]

参加物

6

反応物 3

HCID 962WaterHCID 2316249-Bromo-9-phenylfluoreneHCID 2724010Lithium acetylide-ethylenediamine (1:1)

生成物 1

HCID 22117537HCID 22117537、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 12679Hexamethylphosphoramide溶媒2 回

実験手順

Lithium acetylenide-ethylenediamine (10 mmol) is added to a dry flask under argon, diluted with 5 mL of HMPA, and cooled to between 0 and 5° C. with stirring. A solution of 8 mmol of 9-bromo-9-phenylfluorene dissolved in 4 mL of HMPA is added slowly to the reaction flask. The reaction mixture is warmed to room temperature and, after 2 h, 25 mL of water is slowly added. The mixture is taken up in 100 mL of ether and washed with 20mL of H2O, 20 mL of brine, dried (Na2SO4) and concentrated. The product is purified by chromatography over SiO2 using EtOAc/hexanes (2/98) as eluent. (Smith, W. N.; Beumel, O. F., Preparation of Alkynes with Dialkynes by reaction of monohalo- and dihaloalkanes with lithium acetylenide-ethylenediamine complex., Synthesis, 1974, 441-442.)

後処理

  1. temperaturecooled to between 0 and 5° C.
  2. additionis added slowly to the reaction flask
  3. washwashed with 20mL of H2O, 20 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product is purified by chromatography over SiO2
  7. custom, Preparation of Alkynes with Dialkynes
  8. custom, Synthesis, 1974, 441-442

出典と根拠

ORDレコード
ord-4c246467f63049019e2974f0045eb015
出典データセット
uspto-grants-2000_12
特許番号
US06162824

反応ノート

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