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

HRID 1039151ノート

反応式

HRID 1039151 の反応式
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(OCC)(=O)C.O.C(O)CCC>[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

参加物

8

反応物 4

HCID 105532-Methyl-2-buteneHCID 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 2631-Butanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 tent-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-8fc806c88b094309b6d42f5c3a25edc0
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

反応ノート

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