Pyridine → HCID 19391853, compound

HRID 1756872Notes

Reaction equation

HRID 1756872 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][C:7]([C:10]1[CH:15]=[C:14]([SH:16])[CH:13]=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:21])([CH3:9])[CH3:8].N1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:9][C:7]([C:10]1[CH:15]=[C:14]([S:16][CH2:2][C:3](=[O:5])[CH3:4])[CH:13]=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:21])([CH3:6])[CH3:8]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 6571Chloroacetone2×HCID 11430Potassium CarbonateHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 19391853HCID 19391853, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetone (2.0 mL, 25.2 mM) is added to a 0° C. of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.0 g, 12.6 mM) and pyridine (2.0 mL, 25.2 mM) in methylene chloride (100 mL). The reaction mixture is allowed to warm to room temperature then cooled again to 0° C., and an additional amount of chloroacetone (2.0 mL, 25.2 mM) and pyridine (2.0 mL, 25.2 mM) is added along with K2CO3 (100 mg). The reaction mixture is again allowed to warm to room temperature. The mixture is diluted with ethyl acetate and washed once with dilute aqueous hydrochloric acid, four times with water, and once with brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is crystallized from ethyl acetate:hexane to give 2.8 g (75.5%) of white crystals, mp 105°-106° C.

Workup

  1. temperaturethen cooled again to 0° C.
  2. temperatureto warm to room temperature
  3. washwashed once with dilute aqueous hydrochloric acid, four times with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ea5234a2db2948aa8c64577510410f09
Source dataset
uspto-grants-1995_08
Patent number
US05442111

Reaction notes

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