Hydrochloric Acid → HCID 66999647, compound

HRID 558081

Reaction equation

HRID 558081 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 66999647HCID 66999647, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 2733225Ytterbium triflateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-d93366eab9da4935821bb2614a02f727
Source dataset
uspto-grants-2011_11
Patent number
US08063037B2

Linked notes

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