Potassium Carbonate → HCID 57523004, compound

HRID 1746346Notes

Reaction equation

HRID 1746346 reaction equation
O[CH2:2][C@H:3]1[O:5][C@H:4]1[C@H:6]([O:15][CH2:16][O:17][CH3:18])[CH2:7][C:8](=[CH2:14])[C:9]([O:11][CH2:12]C)=[O:10].[C:19]([O-])([O-])=O.[K+].[K+].C(C(CC)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-])C>CS(C)=O.CO.C(OCC)C>[C:2]([C@H:3]1[O:5][C@H:4]1[C@H:6]([O:15][CH2:16][O:17][CH3:18])[CH2:7][C:8](=[CH2:14])[C:9]([O:11][CH3:12])=[O:10])#[CH:19]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 57523002HCID 57523002, compoundHCID 131733544HCID 131733544, compound

Product 1

HCID 57523004HCID 57523004, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of epoxy alcohol 12 (1.4 g, 4 mmol) in DMSO (5 mL) in a round-bottomed flask was added IBX (1.68 g, 6 mmol) in one portion and the reaction mixture was stirred for 1 h at ambient temperature (25° C.). The reaction mixture was quenched with diethylether (5 mL), H2O (0.5 mL) and filtered through a pad of celite. The residue was repeatedly washed with diethyl ether (50 mL). The filtrate was washed with H2O, brine, dried (Na2SO4) and concentrated to give the crude aldehyde, which was pure enough and used in the next step without further purification. To a solution of crude aldehyde and K2CO3 (900 mg, 8 mmol) in 20 mL dry MeOH and diethyl-1-diazo-2-oxopropylphosphonate (1.26 g, 6 mmol) were added under continuous stirring till completion of the reaction was indicated by TLC (2 h) (25° C.). The reaction mixture was diluted with diethylether (100 mL), washed with aq. solution of NaHCO3 and dried over Na2SO4. Evaporation of solvent yielded analytically pure terminal alkyne 13

Workup

  1. customThe reaction mixture was quenched with diethylether (5 mL), H2O (0.5 mL)
  2. filtrationfiltered through a pad of celite
  3. washThe residue was repeatedly washed with diethyl ether (50 mL)
  4. washThe filtrate was washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give the crude aldehyde, which
  8. customused in the next step without further purification
  9. stirringunder continuous stirring till completion of the reaction
  10. customwas indicated by TLC (2 h) (25° C.)
  11. washwashed with aq. solution of NaHCO3
  12. dry with materialdried over Na2SO4
  13. customEvaporation of solvent

Sources & evidence

ORD record
ord-a6558e80552f4fec981ef474ff284b21
Source dataset
uspto-grants-2015_10
Patent number
US09150498B2

Reaction notes

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