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Hydrochloric Acid → methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate

HRID 1169320
ノート
印刷プレビュー

反応式

HRID 1169320 の反応式
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:19]=[CH:18][C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C[O-].[Na+].Cl.[C:26](=O)([O:29]C)[O:27][CH3:28]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:19]=[CH:18][C:11]3[CH2:12][CH2:13][CH2:14][CH:15]([C:26]([O:27][CH3:28])=[O:29])[C:16](=[O:17])[C:10]=3[CH:9]=2)=[CH:20][CH:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 22990062HCID 22990062、化合物

生成物 1

HCID 22990087methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate収率 88%

反応条件

温度
110 °C

実験手順

To 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (2.67 g, 9.52 mmol) dissolved in dimethyl carbonate (40 ml) was added sodium methoxide (2.57 g, 47.6 mmol), and the resulting mixture was stirred at reflux with heating (110° C.) for 6 hours. The reaction mixture was mixed with 1 N hydrochloric acid (60 ml) under ice cooling and was concentrated under reduced pressure to remove the organic solvent, and then the aqueous layer was extracted with ethyl acetate (30 ml×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 40 g, ethyl acetate/hexane=1/30). The objective fractions were concentrated under reduced pressure to obtain methyl 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate (2.84 g, 8.39 mmol, 88%).

後処理

  1. temperatureat reflux
  2. concentrationwas concentrated under reduced pressure
  3. customto remove the organic solvent
  4. extractionthe aqueous layer was extracted with ethyl acetate (30 ml×3)
  5. dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
  6. concentrationwere then concentrated under reduced pressure
  7. concentrationThe objective fractions were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-c265f7205f544f979fa75dbb6d141209
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06627651B1

反応ノート

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