2-Methyl-2-butene → 7-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanoic acid

HRID 1616537Notes

Reaction equation

HRID 1616537 reaction equation
CC(=CC)C.Cl[O-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[O:29])[S:20][CH:21]=2)=[CH:13][CH:12]=1.P([O-])(O)(O)=[O:31].[K+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:18]=[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:31])=[O:29])[S:20][CH:21]=2)=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphateHCID 23665760Sodium HypochloriteHCID 593240777-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanal

Product 1

HCID 593240787-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanoic acidYield 92.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 2-methyl-2-butene (7.0 mL) and sodium hypochlorite (2.51 g, 27.75 mmol) to a solution of 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptanal (4.02 g, 13.25 mmol) and potassium dihydrogen phosphate (3.10 g, 22.78 mmol) in tert-butanol (60 mL) and water (12 mL) at room temperature. Stir the mixture for 40 minutes, dilute with ethyl acetate (500 mL) and wash with brine (3×200 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with methanol/methylene chloride (1:19), and triturate the residue with hexanes/methylene chloride to afford 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptanoic acid (3.91 g, 88%): APCI MS m/z 320 [C17H21NO3S+H]+.

Workup

  1. washwash with brine (3×200 mL)
  2. dry with materialDry the combined organic extracts over sodium sulfate
  3. customremove the solvent under reduced pressure
  4. customPurify the residue by flash column chromatography on silica gel
  5. washeluting with methanol/methylene chloride (1:19)
  6. customtriturate the residue with hexanes/methylene chloride

Sources & evidence

ORD record
ord-59167aefc3ac472fb1aa1db6446d28fb
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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