Hydrochloric Acid → HCID 16103482, compound

HRID 83961Notes

Reaction equation

HRID 83961 reaction equation
[CH2:1]([C:7]1[C:8]2[S:19][CH:18]=[CH:17][C:9]=2[S:10][C:11]=1[C:12]([O:14]CC)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Li+].[OH-].C1COCC1.Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH2:1]([C:7]1[C:8]2[S:19][CH:18]=[CH:17][C:9]=2[S:10][C:11]=1[C:12]([OH:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 16103450HCID 16103450, compound

Product 1

HCID 16103482HCID 16103482, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Procedure

Compound 61 (32.1 g, 0.11 mol) is mixed with LiOH (10% in water, 50 mL), THF (100 mL), MeOH (30 mL) and a catalytic amount (˜20 mg) tetrabutylammonium iodide in a 500 mL flask. This mixture is heated at reflux overnight, allowed to cool to room temperature, and acidified with concentrated HCl. The resultant yellow solid is collected by filtration and washed thoroughly with water. The solid then is heated with hexane (100 mL) allowed to cool to room temperature. After filtration, the solid is collected, dried over vacuum to yield compound 62 as a light yellow powder (28.0 g, 96.7% yield). M.P.: 110.7-112.4° C.

Workup

  1. temperatureThis mixture is heated
  2. temperatureat reflux overnight
  3. filtrationThe resultant yellow solid is collected by filtration
  4. washwashed thoroughly with water
  5. temperatureThe solid then is heated with hexane (100 mL)
  6. temperatureto cool to room temperature
  7. filtrationAfter filtration
  8. customthe solid is collected
  9. customdried over vacuum

Sources & evidence

ORD record
ord-703686e01fb24bfbb9d6aee3ac409731
Source dataset
uspto-grants-2014_09
Patent number
US08846855B2

Reaction notes

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