Methyl Thioglycolate → HCID 19828249, compound

HRID 1494439Notes

Reaction equation

HRID 1494439 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH:11]([OH:16])[CH2:10][C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19](OC)(=[O:22])[CH2:20][SH:21].[NH2-].[Li+]>C1(C)C=CC=CC=1>[C:19]([O:16][CH:11]1[CH2:10][C:9]([CH3:18])([CH3:17])[N:8]([O:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:13]([CH3:14])([CH3:15])[CH2:12]1)(=[O:22])[CH2:20][SH:21]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 24532Lithium amideHCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

Product 1

HCID 19828249HCID 19828249, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-ol a (25.5 grams, 0.1 mol) and methyl thioglycolate (10.6 grams, 0.11 mol) are dissolved in toluene. Lithium amide (0.09 mol) is added and the reaction mixture is heated under reflux and the distillate collected in a Dean-Stark trap. After heating under reflux overnight, the toluene is removed under reduced pressure. Acetic acid is added to neutralize the basic catalyst. The crude reaction product is purified by liquid chromatography to afford the title compound.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux
  3. distillationthe distillate collected in a Dean-Stark trap
  4. temperatureAfter heating
  5. temperatureunder reflux overnight
  6. customthe toluene is removed under reduced pressure
  7. additionAcetic acid is added
  8. customThe crude reaction product
  9. customis purified by liquid chromatography

Sources & evidence

ORD record
ord-2953087d3daf445a9af5f927cbeffd61
Source dataset
uspto-grants-1991_06
Patent number
US05026750

Reaction notes

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