Sulfuric Acid → 1-(4-Methoxynaphthyl)-octan-1,2-dione 2-oxime

HRID 498140

반응식

HRID 498140 반응식
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:5][CH:4]=1.[N:22](OC)=[O:23].OS(O)(=O)=O.N([O-])=O.[Na+]>CO.O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](=[O:21])[C:14](=[N:22][OH:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:5][CH:4]=1

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 12231Methyl nitriteHCID 223208401-(4-Methoxynaphthyl)-octan-1-oneHCID 23668193Sodium Nitrite

생성물 1

HCID 738823721-(4-Methoxynaphthyl)-octan-1,2-dione 2-oxime

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 21226206Ethyl acetate hexane용매

실험 절차

10.0 g (35.2 mmol) of 1-(4-methoxynaphthyl)-octan-1-one are dissolved in 35 mL of t-butyl methyl ether. HCl-gas is introduced into this solution under cooling in an ice bath, and methyl nitrite-gas, which is genarated by adding H2SO4 aq. solution (3.5 mL of conc. H2SO4 and 7 mL of H2O ) into NaNO2 (3.65 g, 52.7 mmol) in methanol (3 mL) and H2O (3 mL), is introduced for 10 min at an ice-bath temperature. Then, the reaction solution is poured into ice, and the crude product is extracted with t-butyl methyl ether. This ether layer is washed with saturated NaHCO3 aq. solution and brine, dried over anhydrous MgSO4, and then condensed. The residue is applied to column chromatography on silica gel with ethyl acetate-hexane (10:90) as eluent. 2.02 g of yellow solid are obtained (18%). M.p. 92-93° C. 1H-NMR spectrum (CDCl3). δ [ppm]: 0.90 (t, 3H), 1.31-1.55 (m, 6H), 1.59-1.65 (m , 2H), 2.79 (t,2H), 4.06 (s, 3H), 6.80 (d, 1H), 7.51 (t, 1H), 7.58 (t, 1H), 7.72 (d, 1H), 7.75 (d, 1H), 8.33 (d, 1H), 8.44 (d, 1H).

후처리

  1. additionis introduced into this solution
  2. temperatureunder cooling in an ice bath
  3. additionis introduced for 10 min at an ice-bath temperature
  4. additionThen, the reaction solution is poured into ice
  5. extractionthe crude product is extracted with t-butyl methyl ether
  6. washThis ether layer is washed with saturated NaHCO3 aq. solution and brine
  7. dry with materialdried over anhydrous MgSO4
  8. customcondensed

출처 및 근거

ORD 기록
ord-b3cd28d7bbf749c69f5d3ff833507ba3
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949678B2

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