Hydrochloric Acid → HCID 14852026, compound

HRID 1032829Notes

Reaction equation

HRID 1032829 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[K+].[C:9]([C:13]1[CH:14]=[C:15]([NH:24][C:25](=[O:29])[CH:26]=[CH:27][CH3:28])[CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])([CH3:12])([CH3:11])[CH3:10].Cl>O1CCCC1.C(O)C>[C:20]([C:17]1[CH:16]=[C:15]([N:24]2[CH2:28][CH:27]([CH3:2])[CH2:26][C:25]2=[O:29])[CH:14]=[C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])[C:18]=1[OH:19])([CH3:21])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 82127Potassium hydrideHCID 54505295HCID 54505295, compound

Product 1

HCID 14852026HCID 14852026, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Trimethyl sulphoxonium iodide (5.9 g, 27 mmol) was added to 5.2 g (45 mmol) of 35% potassium hydride in an oil dispersion (previously washed with pentane) in 25 ml of tetrahydrofuran at 0° C. Ten minutes later, 5.2 g (18 mmol) of N-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-butenamide dissolved in 100 ml of tetrahydrofuran was added and the mixture was allowed to warm to room temperature. Twenty four hours later, 10 ml of ethanol was added and the mixture was made acidic by the addition of 1N hydrochloric acid. The acidic mixture was concentrated to 50 ml, diluted with 100 ml of ethyl acetate and 50 ml of water and the organic phase was separated, dried over anhydrous magnesium sulfate and concentrated to a solid. The solid was chromatographed on silica gel with methylene chloride and triturated in pentane to afford 0.76 g of 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methylpyrrolidin-2-one, mp 157°-159° C.

Workup

  1. washpreviously washed with pentane) in 25 ml of tetrahydrofuran at 0° C
  2. additionwas added
  3. concentrationThe acidic mixture was concentrated to 50 ml
  4. additiondiluted with 100 ml of ethyl acetate and 50 ml of water
  5. customthe organic phase was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to a solid
  8. customThe solid was chromatographed on silica gel with methylene chloride
  9. customtriturated in pentane

Sources & evidence

ORD record
ord-5385da49de3241c28b819e58c1420d11
Source dataset
uspto-grants-1990_09
Patent number
US04959482

Reaction notes

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