m-Chloroperbenzoic acid → HCID 18330057, 화합물

HRID 2271040노트

반응식

HRID 2271040 반응식
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=C(Cl)C=C(C(OO)=[O:22])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:22]1[C:10]2[CH2:9][CH2:8][C:7]3[C:12]([C:11]1=2)=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14566727HCID 14566727, 화합물

생성물 1

HCID 18330057HCID 18330057, 화합물수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 7-nitro-3,4-dihydronaphthalene (9.18 g; 0.052 mol) (from Preparation 2) in CH2Cl2 (600 ml) was cooled to 0° C. and treated with m-CPBA, 57-85%, (13.86 g, approx. 0.056 mol, approx. 1.1 equiv). The reaction mixture was allowed to stir for 48 h, slowly warming to room temperature. The mixture was treated with aqueous NaHCO3 (300 ml) and the organic layer was separated. The organic layer was extracted with additional aqueous NaHCO3, washed with aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure to give 1,2-epoxy-7-nitro-3,4-dihydronaphthalene (9.94, 100%) as a white solid which was used in the next step without further purification. Rf (silica gel): 0.56(70% hexane: 30% EtOAc); 1H NMR (300 MHZ, CDCl3) 8.24 (s, 1H), 8.08 (dd, J=1.8 and 8.1 H 1H), 7.23 (d, J=8.1 Hz, 1H), 3.92 (d, J=4.2 Hz, 1H), 3.77 (s, 1H), 2.87-2.62 (m, 2H), 2.47 (dd, J=6.6 and 14.4 Hz, 1H), 1.78 (dt, J=5.7 and 14.1 Hz, 1H), 13C NMR (75 MHZ, CDCl3) 146.5, 144.7, 134.5, 129.4, 124.4, 123.4, 54.7, 51.8, 24.5, 21.0.

후처리

  1. customthe organic layer was separated
  2. extractionThe organic layer was extracted with additional aqueous NaHCO3
  3. washwashed with aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-92c4c509bb4a4f17a0dd12253a0dfc66
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06333337B1

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