Tetraethyltin → 2-ethyl-10,11-dihydro-5H-dibenzo [a,d]cyclohepten-5-one

HRID 1275915Notes

Reaction equation

HRID 1275915 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH2:18]([Sn](CC)(CC)CC)[CH3:19]>CN(C)C=O.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>[CH2:18]([C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1)[CH3:19]

Participants

5

Reactant 2

HCID 11704TetraethyltinHCID 192617812-Bromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 221172892-ethyl-10,11-dihydro-5H-dibenzo [a,d]cyclohepten-5-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of the product from step (iv) (1.52 g), tetraethyl tin (10.4 ml) and tetrakis(triphenylphosphine)palladium(0) (100 mg) in dimethylformamide (20 ml) was heated at 130° C. for 48 hours. The mixture was evaporated and the residue purified by chromatography eluting with isohexane then 50% toluene in isohexane then toluene. Yield 0.88 g.

Workup

  1. customThe mixture was evaporated
  2. customthe residue purified by chromatography
  3. washeluting with isohexane

Sources & evidence

ORD record
ord-fef0f6e46a054941975ac4b93e1e766f
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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