Tributylstannane → HCID 12621140, compound

HRID 372088Notes

Reaction equation

HRID 372088 reaction equation
Br[C:2]12[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH:9]3[CH:16](Br)[C:6]1([C:7]1[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=13)[CH2:5][N:4]([CH3:22])[C:3]2=[O:23].C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1>[CH3:22][N:4]1[CH2:5][C:6]23[CH2:16][CH:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[CH:2]2[C:3]1=[O:23])[C:8]1[CH:18]=[CH:19][CH:20]=[CH:21][C:7]3=1

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 12621139HCID 12621139, compound

Product 1

HCID 12621140HCID 12621140, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 8.07 g of 1a, 17.2 g of freshly distilled tributyltin hydride and 50 ml of anhydrous benzene is heated under reflux under nitrogen for 3 days. Most of the benzene is removed and the residue is distilled through a short-path column (to 125° bath temperature, 1 micron). The pot residue is crystallized from isopropyl alcohol to give 3,63 g (71% yield) of 2-methyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrol-1-one (1b), mp 141°-146°. A sample crystallized once from isopropyl alcohol has mp 147°-157°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux under nitrogen for 3 days
  3. customMost of the benzene is removed
  4. distillationthe residue is distilled through a short-path column (to 125° bath temperature, 1 micron)
  5. customThe pot residue is crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-23cf7090135c43e89ea4851707064297
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

Loading…