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

HRID 505701노트

반응식

HRID 505701 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9fac2d9edb0545da8095f7947b4aa171
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781428B2

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