Hydrochloric Acid → HCID 66999647, 화합물

HRID 558081

반응식

HRID 558081 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[CH:10][C:9]3[C:12]([CH3:16])=[CH:13][CH:14]=[CH:15][C:8]=3[O:7][C:6]=2[CH:17]=1.CO/[CH:20]=[CH:21]/[C:22]([O:24][Si](C)(C)C)=[CH2:23].C1COCC1.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:20]=[CH:21][C:22](=[O:24])[CH2:23][CH:10]3[C:9]3[C:12]([CH3:16])=[CH:13][CH:14]=[CH:15][C:8]=3[O:7][C:6]=2[CH:17]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 5366448trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadieneHCID 66999466HCID 66999466, 화합물

생성물 1

HCID 66999647HCID 66999647, 화합물수율 82%

시약·촉매·용매 3

HCID 2733225Ytterbium triflate촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-bromo-1-methyldibenz[b,f][1,4]oxazepine (25.05 g, 86.98 mmol) and Ytterbium(III) triflate (2.8 g, 4.5 mmol) in toluene (0.21 L) at 0° C., (E)-1-methoxy-3-trimethylsilyloxy-1,3-butadiene (18 mL, 95.7 mmol) was added dropwise. THF (0.1 L) was added to dissolve the formed precipitate and the solution was stirred for 15 min. 1N hydrochloric acid (50 mL) was added and the resulting mixture was stirred for an additional 15 min, after which it was diluted with ethyl acetate and washed with brine. After drying (Na2SO4) the solvent was evaporated under reduced pressure to yield the crude compound which was triturated in methanol to give the title compound (25.4 g, 82%). Data: 1H-NMR (400 MHz, CDCl3) δ 2.31 (s, 3H), 2.43 (m, 1H), 3.00 (m, 1H), 5.23 (m, 1H), 5.41 (m, 1H), 6.99-7.52 (m, 7H). (m/z)=356+358 (M+H)+.

후처리

  1. dissolutionto dissolve the formed precipitate
  2. stirringthe resulting mixture was stirred for an additional 15 min
  3. washwashed with brine
  4. dry with materialAfter drying (Na2SO4) the solvent
  5. customwas evaporated under reduced pressure
  6. customto yield the crude compound which
  7. customwas triturated in methanol

출처 및 근거

ORD 기록
ord-d93366eab9da4935821bb2614a02f727
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063037B2

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