Oxalyl chloride → Methyl 3-hydroxynaphthalene-1-carboxylate

HRID 2185885

反応式

HRID 2185885 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:15](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 1902323-Hydroxy-1-naphthoic acid

生成物 1

HCID 23423090Methyl 3-hydroxynaphthalene-1-carboxylate収率 35%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 3-hydroxy-1-naphthalenecarboxylic acid (6.67 g, 35.4 mmol) and oxalyl chloride (3.86 mL, 44.2 mmol) in DCM (150 mL) was added 3 drops of DMF. The mixture was stirred at room temperature for 3 h., the solvent was removed under reduced pressure and methanol (150 mL) was added. After stirring at reflux for 15 min the solvent was removed under reduced pressure, the residue was purified by column chromatography (10%, 20% and 30% EtOAc/hexane) to give the title compound as a yellow solid (2.5 g, 35%). 1H NMR (DMSO-d6) δ 10.10 (s, 1H), 8.61 (d, 1H), 7.77 (d, 1H), 7.72 (d, 1H), 7.47 (m, 2H), 7.38 (d, 1H), 3.93 (s, 3H); MS m/z 201.1 (M−H).

後処理

  1. customthe solvent was removed under reduced pressure and methanol (150 mL)
  2. additionwas added
  3. stirringAfter stirring
  4. temperatureat reflux for 15 min the solvent
  5. customwas removed under reduced pressure
  6. customthe residue was purified by column chromatography (10%, 20% and 30% EtOAc/hexane)

出典と根拠

ORDレコード
ord-6f31a575f07b468da6155b9f28e6b5a0
出典データセット
uspto-grants-2002_06
特許番号
US06403601B1

関連ノート

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