Sulfuric Acid → Methyl 7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1640113ノート

反応式

HRID 1640113 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:14]([O:16][CH3:17])=[O:15])[C:10]2=O)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[H][H]>[Pd].CC(O)=O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)=[CH:5][CH:4]=1

参加物

7

反応物 3

HCID 1118Sulfuric AcidHCID 14722817Methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 13058284Methyl 7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate収率 71%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

実験手順

A slurry of methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (6.0 g, 26 mmol) and 10% palladium on carbon (100 mg) in AcOH (120 mL), and concentrated sulfuric acid (780 μL) was allowed to stir under 30 psi of hydrogen for 2.5 h. The reaction mixture was diluted with chloroform, and filtered through Celite. The filtrate was washed with water (5×), dried over Na2SO4 and evaporated. The residue was purified by filtration through a pad of silica, to give methyl 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylate as an oil (4.03 g, 71%). 1H NMR (300 MHz, CD3OD): δ 6.94 (d, 1H), 6.67-6.62 (m, 2H), 3.72 (s, 3H), 3.69 (s, 3H), 2.94-2.91 (m, 2H), 2.78-2.70 (m, 3H), and 2.18-2.09 (m, 1H), and 1.86-1.73 (m, 1H).

後処理

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with water (5×)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. filtrationThe residue was purified by filtration through a pad of silica

出典と根拠

ORDレコード
ord-0db14d2d357b47daa9112ca49aea7d90
出典データセット
uspto-grants-2012_02
特許番号
US08110687B2

反応ノート

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