Oxalyl chloride → Methyl 3-hydroxynaphthalene-1-carboxylate

HRID 2185885

반응식

HRID 2185885 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 23423090Methyl 3-hydroxynaphthalene-1-carboxylate수율 35%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6f31a575f07b468da6155b9f28e6b5a0
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403601B1

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