Monobasic potassium phosphate → 7-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanoic acid

HRID 1443650Notes

Reaction equation

HRID 1443650 reaction equation
Cl[O-].[Na+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])[S:15][CH:16]=2)=[CH:8][CH:7]=1.P([O-])(O)(O)=[O:26].[K+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:26])=[O:24])[S:15][CH:16]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 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-27-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-e1866ce6c2e84914a47d010d14876ffa
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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