Sulfuric Acid → Ethyl 1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxylate

HRID 494439노트

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HRID 494439 반응식
[C:1]1([C:7]([CH2:24][CH2:25][CH3:26])([CH2:21][CH2:22][CH3:23])[C:8]([CH:10]([C:16](OCC)=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>O>[OH:17][C:16]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:7]([CH2:24][CH2:25][CH3:26])([CH2:21][CH2:22][CH3:23])[C:8](=[O:9])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 11552281Diethyl 2-(2-phenyl-2-propylpentanoyl)malonate

생성물 1

HCID 54724640Ethyl 1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxylate수율 44.1%

시약·촉매·용매 1

HCID 962Water용매

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온도
25 °C

실험 절차

The product of Example 1E (4.51 g, 12.4 mmol) was treated with concentrated sulfuric acid (25 mL) and stirred at 25° C. for 3 hours. The mixture was then poured into a mixture of ice and water (500 mL) and stirred until all the ice melted. The mixture was extracted with ethyl acetate (2×). The combined organic layers were washed with water and saturated sodium chloride solution, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with methyl t-butyl ether in hexane to afford the title compound (1.73 g, 44%). 1H NMR (300 MHz, CDCl3): δ 15.15 (d, J=13.24 Hz, 1 H), 8.18 (m, 1 H), 7.59 (m, 1 H), 7.40 (m, 2 H), 4.47 (m, 2 H), 2.25 (m, 2 H), 1.91 (m, 1H), 1.70 (m, 1 H), 1.47 (q, J=7.23 Hz, 3 H), 1.25 (m, 1 H), 0.93 (m, 2 H), 0.67 (m, 7 H).

후처리

  1. extractionThe mixture was extracted with ethyl acetate (2×)
  2. washThe combined organic layers were washed with water and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluting with methyl t-butyl ether in hexane

출처 및 근거

ORD 기록
ord-45898439cd334ccbbc74c0848fa835ae
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

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