p-Toluenesulfonic acid monohydrate → HCID 14566727, 화합물

HRID 2271039노트

반응식

HRID 2271039 반응식
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10](O)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(O)(C1C=CC(C)=CC=1)(=O)=O.O>C1(C)C=CC=CC=1>[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]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 183300457-Nitro-1,2,3,4-tetrahydronaphthalen-2-ol

생성물 1

HCID 14566727HCID 14566727, 화합물수율 100%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

7-nitro-1,2,3,4-tetrahydo-2-naphthalenol (10.13 g, 0.053 mol) (from Preparation 1) was heated in the presence of TsOH—H2O (1.72 g, 0.009 mol, 0.2 equiv.) in toluene (150 ml) for 2 h at 100° C. The solvent was removed under reduced pressure and the residue was treated with EtOAc (150 ml) and saturated aqueous NaHCO3 (150 ml). The aqueous layer was separated and extracted with additional EtOAc (2×100 ml). The combined organic layers were washed with saturated aqueous NaCl (200 ml), dried (Na2SO4), filtered, and concentrated under reduced pressure to give 7-nitro-3,4-dihydronaphthalene as a brown oil (9.18 g, 100%) which was used in the next step without additional purification. Rf (silica gel): 0.79 (70% hexane: 30% EtOAc); 1H NMR (300 MHZ, CDCl3) 7.95 (dd, J=2.4 and 8.1 Hz, 1H), 7.83 (d, J=2.4 Hz, 1H), 7.21 (d, J=8.1 Hz, 1H), 6.50 (d, J=6.50 Hz, 1H), 6.18 (dt, J=4.5 and 9.6 Hz, 2H), 2.88 (t, J=8.4 Hz, 2H), 2.40-2.34 (m, 2H); 13C NMR (75 MHZ, CDCl3) 147.1, 143.1, 135.3, 131.4, 128.2, 126.5, 121.8, 120.3, 27.4, 22.5.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was treated with EtOAc (150 ml) and saturated aqueous NaHCO3 (150 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with additional EtOAc (2×100 ml)
  5. washThe combined organic layers were washed with saturated aqueous NaCl (200 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-21b3215ea7714b54a7725a8fb0096a79
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06333337B1

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