Sodium hydride → Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate

HRID 1244649

反応式

HRID 1244649 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C)C=O.O1CCCC1>[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2

参加物

6

反応物 3

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

生成物 1

HCID 12085484Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

14 g (69 mmol) of methyl 6-hydroxynaph-thalene-2-carboxylate in 90 ml of dimethylformamide and 90 ml of tetrahydrofuran are introduced into a round-bottomed flask and under a nitrogen stream. 3.3 g (82 mmol) of sodium hydride at 60% are added in small portions. When the gas emission has ceased, 8.7 ml (76 mmol) of 2-methoxyethoxymethyl chloride are added and the reaction medium is stirred for 3 hours at room temperature. It is then poured into ice-cold water and extracted with ether. The organic phase is dried over magnesium sulphate, filtered and evaporated off. The residue obtained is purified by chromatography on a silica column eluted with a heptane and ethyl acetate (80/20) mixture and 17 g (85%) of the expected product are obtained in the form of a colorless oil.

後処理

  1. additionIt is then poured into ice-cold water
  2. extractionextracted with ether
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated off
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a heptane and ethyl acetate (80/20) mixture and 17 g (85%) of the expected product
  9. customare obtained in the form of a colorless oil

出典と根拠

ORDレコード
ord-48ba0cf758bc4273affe91007eb69bc0
出典データセット
uspto-grants-2006_10
特許番号
US07122564B2

関連ノート

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