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

HRID 1443650ノート

反応式

HRID 1443650 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-e1866ce6c2e84914a47d010d14876ffa
出典データセット
uspto-grants-2010_02
特許番号
US07662771B2

反応ノート

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