Tetrahydrofuran → Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate

HRID 1245427

反応式

HRID 1245427 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2.O1CCCC1.[CH3:23][O:24][CH2:25][CH2:26][O:27][CH2:28]Cl>CN(C)C=O>[CH3:23][O:24][CH2:25][CH2:26][O:27][CH2:28][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 390995Methyl 6-hydroxy-2-naphthoate

生成物 1

HCID 12085484Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3.3 g (83 mmol) of 60% sodium hydride in oil are added portionwise to a solution of 14 g (69 mmol) of methyl 6-hydroxynaphthalene-2-carboxylate in 180 ml of an equivolume mixture of tetrahydrofuran and dimethylformamide. After the evolution of gas has ceased, 8.7 ml (76 mmol) of methoxyethoxymethyl chloride are added dropwise. The reaction medium is stirred at room temperature for 3 hours, immersed into ice-cold water and extracted with ethyl ether. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 17 g of methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate are obtained in the form of a colorless oil, in a yield of 85%.

後処理

  1. extractionextracted with ethyl ether
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with an 80/20 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-561eae2879104e1584fc2cf404214913
出典データセット
uspto-grants-2006_10
特許番号
US07125869B2

関連ノート

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