Tributylstannane → HCID 19434456, compound

HRID 1735862Notes

Reaction equation

HRID 1735862 reaction equation
Br[CH:2]([C:5]1([O:20][CH2:21][CH3:22])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)[CH2:3][OH:4].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[CH2:21]([O:20][C:5]1([CH2:2][CH2:3][OH:4])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)[CH3:22]

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 19079050HCID 19079050, compound

Product 1

HCID 19434456HCID 19434456, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 1140TolueneSolvent

Procedure

Dissolved 2-bromo-2-[6,11-dihydro-11-ethoxy-dibenz[b,e]oxepin-11-yl]-ethanol (14.34 g, 0.0395 mol) in 150 mL of dry toluene. Added tri-n-butyl tin hydride (17.24 g, 15.9 mL, 0.0592 mol) and AIBN (0.324 g, 0.00197 mol). Refluxed under a nitrogen atmosphere for 18 hours. Cooled to room temperature, and evaporated. Dissolved residue in 300 mL of acetonitrile, and washed with hexane to remove tin by-products. Dried acetonitrile solution with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate:hexane then 1:3 ethyl acetate:hexane. Combined appropriate fractions, and evaporated to give 6.22 g (55% yield) of 2-[6,11-dihydro-11-ethoxydibenz[b,e]oxepin-11-yl]-ethanol as a colorless oil.

Workup

  1. temperatureRefluxed under a nitrogen atmosphere for 18 hours
  2. customevaporated
  3. washDissolved residue in 300 mL of acetonitrile, and washed with hexane
  4. customto remove tin by-products
  5. filtrationDried acetonitrile solution with MgSO4, filtered
  6. customevaporated
  7. customPurified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate
  8. customevaporated

Sources & evidence

ORD record
ord-f0188ec914394c73a988da9d172cf04c
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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