Acetylene → HCID 21308562, compound

HRID 1419631Notes

Reaction equation

HRID 1419631 reaction equation
C#C.[CH2:3]([Li])[CH2:4]CC.[CH3:8][Si:9]([CH3:31])([C:27]([CH3:30])([CH3:29])[CH3:28])[O:10][C@H:11]1[CH2:16][C@H:15]([O:17][Si:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][C:13](=[O:25])[CH:12]1[CH3:26]>C1COCC1>[CH3:31][Si:9]([CH3:8])([C:27]([CH3:30])([CH3:29])[CH3:28])[O:10][C@H:11]1[CH2:16][C@H:15]([O:17][Si:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][C:13]([C:3]#[CH:4])([OH:25])[CH:12]1[CH3:26]

Participants

5

Reactant 3

HCID 6326AcetyleneHCID 67592243HCID 67592243, compoundHCID 178418339Butyllithium

Product 1

HCID 21308562HCID 21308562, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., acetylene is introduced into 50 ml of THF for 20 minutes. 1.25 ml n-Butyllithium solution (1.6M in hexane, 2 mmol) is added in drops and stirred for 20 more minutes at this temperature. Then, 215 mg (0.58 mmol) of 9 in 2 ml of THF is added in drops and stirred for 2 hours. Then, it is quenched with saturated ammonium chloride solution, diluted with ethyl acetate, and the organic phase is washed with saturated sodium chloride solution, dried on sodium sulfate and the solvent is removed. The residue is purified on silica gel by column chromatography (mobile solvent: EE:H=4:6, Rf =0.6), whereby 163 mg (0.41 mmol) of title compound 10 is obtained as a white crystalline substance.

Workup

  1. stirringstirred for 2 hours
  2. customThen, it is quenched with saturated ammonium chloride solution
  3. additiondiluted with ethyl acetate
  4. washthe organic phase is washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. customthe solvent is removed
  7. customThe residue is purified on silica gel by column chromatography (mobile solvent: EE:H=4:6, Rf =0.6)

Sources & evidence

ORD record
ord-de02e5f707f5431a92d912a7605923b2
Source dataset
uspto-grants-1999_03
Patent number
US05886233

Reaction notes

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