Methanol → Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

HRID 505701ノート

反応式

HRID 505701 の反応式
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]1=2.[CH3:15]O>Cl>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2

参加物

4

反応物 2

HCID 887MethanolHCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

生成物 1

HCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate収率 86%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A solution of 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (5.14 g, 27.0 mmol) (Peakdale Molecular) in 4N hydrochloric acid in methanol was heated to reflux for eighteen hours. The solution was returned to ambient temperature and concentrated in vacuo. The residue was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution and saturated sodium chloride and dried over magnesium sulfate. Filtration followed by concentration in vacuo provided methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate as a brown solid (4.76 g, 86% yield). Reversed-phase HPLC on 4.6×50 mm C-18 column, tR=1.90 minutes (10 to 90% acetonitrile/water over 4 minutes at 4 mL/minute with detection 254 nm, at 20° C.); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.99-2.08 (m, 2H), 2.58-2.66 (m, 2H), 2.99 (t, J=6.04 Hz, 2H), 3.85 (s, 3H), 7.83-7.87 (m, 1H), 7.91 (d, J=0.81 Hz, 1H), 7.92-7.97 (m, 1H).

後処理

  1. temperatureto reflux for eighteen hours
  2. customwas returned to ambient temperature
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution and saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration
  8. concentrationfollowed by concentration in vacuo

出典と根拠

ORDレコード
ord-9fac2d9edb0545da8095f7947b4aa171
出典データセット
uspto-grants-2010_08
特許番号
US07781428B2

反応ノート

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