Sodium Bicarbonate → HCID 13237261, compound

HRID 2171742Notes

Reaction equation

HRID 2171742 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]#[C:5][CH:6]([OH:9])[CH2:7][CH3:8].C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:10])[C:4]#[C:5][C:6](=[O:9])[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 13859766Methyl 4-hydroxyhex-2-ynoate

Product 1

HCID 13237261HCID 13237261, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Hydroxy-hex-2-ynoic acid methyl ester (1.50 g, 10.55 mmol) in dichloromethane (30 mL) was added Des-martin periodinane (6.0 g, 14.14 mmol) and stirred at room temperature for 18 hours. Additional periodinane (4.5 g) was added to the reaction mixture and stirred at room temperature for 6 hours. Aqueous NaHCO3 was added to reaction mixture, and precipitate was filtered and washed with dichloromethane. Aqueous phase was extracted with dichloromethane, and combined organic phase was washed with water, brine, dried over Na2SO4, filtered and concentrated under vacuum to afford 1.48 g (100%) of title compound. C7H8O3 (140.04)

Workup

  1. additionAdditional periodinane (4.5 g) was added to the reaction mixture
  2. stirringstirred at room temperature for 6 hours
  3. filtrationwas filtered
  4. washwashed with dichloromethane
  5. extractionAqueous phase was extracted with dichloromethane, and combined organic phase
  6. washwas washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-41bafedf419747a6bed1a52448213de6
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

Loading…