Water → HCID 22117537, compound

HRID 1275795Notes

Reaction equation

HRID 1275795 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 22117537HCID 22117537, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 12679HexamethylphosphoramideSolvent2×

Procedure

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.)

Workup

  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

Sources & evidence

ORD record
ord-4c246467f63049019e2974f0045eb015
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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