Carbon tetrabromide → Methyl 7-(5-phenyl-1,3-oxazol-2-yl)heptanoate

HRID 1039154ノート

反応式

HRID 1039154 の反応式
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:21])[NH:11][CH2:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:21][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][N:11]=1

参加物

6

反応物 3

HCID 11205Carbon tetrabromide2 回HCID 11776Triphenylphosphine2 回HCID 59167774HCID 59167774、化合物

生成物 1

HCID 59167750Methyl 7-(5-phenyl-1,3-oxazol-2-yl)heptanoate収率 41.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Add a solution of 7-(2-oxo-2-phenylethylcarbamoyl)heptanoic acid methyl ester (7.05 g, 23.1 mmol) and carbon tetrabromide (11.3 g, 34.3 mmol) in methylene chloride over 40 minutes to a mixture of triphenylphosphine (9.0 g, 34.3 mmol) and DMAP (5.51 g, 45.1 mmol) in methylene chloride (500 mL) at room temperature under nitrogen. Stir the mixture for 30 minutes and add additional triphenylphosphine (2.6 g, 9.92 mmol) and carbon tetrabromide (3.35 g, 10.1 mmol). Stir the mixture for an additional 20 minutes, filter through Celite and wash with ethyl acetate (3×100 mL). Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (70:30), to provide 7-(5-phenyloxazol-2-yl)heptanoic acid methyl ester (2.75 g, 41%).

後処理

  1. stirringStir the mixture for an additional 20 minutes
  2. filtrationfilter through Celite
  3. washwash with ethyl acetate (3×100 mL)
  4. customRemove the solvent under reduced pressure
  5. custompurify the residue by flash column chromatography on silica gel
  6. washeluting with hexanes/ethyl acetate (70:30)

出典と根拠

ORDレコード
ord-3ae180d21ed1473a93b9e77a7250a9ab
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

反応ノート

読み込み中…