Tetrahydrofuran → 6-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxy-5-nitronaphthalene

HRID 1582895노트

반응식

HRID 1582895 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](OS(C(F)(F)F)(=O)=O)=[C:10]2[N+:13]([O-:15])=[O:14])=[CH:5][CH:4]=1.C[Sn](C)(C)[C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][C:29]2[O:35][CH2:36][O:37][C:28]=2[CH:27]=1.C1C[O:43][CH2:42]C1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:36]1[O:37][C:28]2[C:29](=[CH:30][C:31]([N+:32]([O-:34])=[O:33])=[C:26]([C:9]3[C:10]([N+:13]([O-:15])=[O:14])=[C:11]4[C:6](=[CH:7][CH:8]=3)[CH:5]=[C:4]([O:43][CH3:42])[C:3]([O:2][CH3:1])=[CH:12]4)[CH:27]=2)[O:35]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 10782610Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannaneHCID 227164357-Methoxy-1-nitro-2-trifluoromethanesulfonyloxynaphthalene

생성물 1

HCID 227164396-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxy-5-nitronaphthalene수율 42%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

Tetrakis(triphenylphosphine)palladium (0) (100 mg) and cuprous bromide (20 mg) was added to a solution of 7-Methoxy-1-nitro-2-trifluoromethanesulfonyloxy-naphthalene 53 (366 mg, 1.04 mmol) and trimethylnitroarylstannane 62 (500 mg, 1.52 mmol) in THF (30 mL) at room temperature and stirred for 0.5 h. The mixture was then refluxed under N2 overnight. After cooling, THF was evaporated and ethyl acetate (30 mL) was added to the residue. The solution was washed with water. The organic layer was separated and passed through a Celite bed to remove suspended particles. The organic layer was then washed with brine, dried (anhydrous Na2SO4), and evaporated in vacuo. The residue was chromatographed using a 70:30 mixture of hexanes:ethyl acetate to give 54 (160 mg) in 42% yield; mp 187-189° C.; IR (KBr) 2925, 1628, 1526, 1487, 1364, 1332, 1265, 1230 cm−1; 1H NMR (CDCl3) δ3.92 (3H, s), 6.19 (2H, d), 6.76 (1H, s), 7.12 (1H, d, J=2.5), 7.18 (1H, d, J=8.3), 7.28 (1H, dd, J1=9.0, J2=2.3), 7.70 (1H, s), 7.85 (1H, d, J=9.2), 7.93 (1H, d, J=8.4), 13C NMR δ56.08, 100.59, 103.93, 106.31, 110.70, 121.54, 124.07, 126.47, 128.71, 129.55, 130.33, 130.99, 131.23, 142.83, 148.92, 152.07, 160.68.

후처리

  1. temperatureThe mixture was then refluxed under N2 overnight
  2. temperatureAfter cooling
  3. customTHF was evaporated
  4. additionethyl acetate (30 mL) was added to the residue
  5. washThe solution was washed with water
  6. customThe organic layer was separated
  7. customto remove
  8. washThe organic layer was then washed with brine
  9. dry with materialdried (anhydrous Na2SO4)
  10. customevaporated in vacuo
  11. customThe residue was chromatographed
  12. additiona 70:30 mixture of hexanes

출처 및 근거

ORD 기록
ord-dbe2ca84eeb44d59b0369fe900b84bdb
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740650B2

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