Tributylstannane → HCID 19897427, compound

HRID 1197179Notes

Reaction equation

HRID 1197179 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2C=CC=[C:12]([C:14]3(C[SeH])CC[CH2:17][O:16][C:15]3=[O:20])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][CH:13]1[CH2:17][O:16][C:15](=[O:20])[CH2:14][CH2:12]1

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 178519100HCID 178519100, compound

Product 1

HCID 19897427HCID 19897427, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

5-(3-Bromophenyl)phenylselenylmethyl-tetrahydropyran-2-one (6.7 g, 15.8 mmole) is suspended in 100 ml dry toluene in an oven dried 250 ml 3-neck round bottom flask under nitrogen. The suspension is brought to solution by warming to 65° C. The solution is treated with tributyltin hydride (4.7 ml, 17.4 mmole), stirred for 10 minutes, and treated with azo(bis)isobutyrlnitrile (0.285 g, 1.74 mmole) in one lot. The reaction mixture is stirred 1.5 hours at 65° C., cooled to room temperature, and concentrated in vacuo to a pale oil. The oil is chromatographed over 250 g silica gel (230-400 mesh), eluting with 20% ethyl acetate/hexane and after a 2500 ml forerun collecting 60 ml fractions. Fractions 10-48 are combined and concentrated to afford 3.45 g of the title compound as a pale oil. Following the above procedures gives the title compound having the physical characteristic described below:

Workup

  1. customdried 250 ml 3-neck round bottom flask under nitrogen
  2. additiontreated with azo(bis)isobutyrlnitrile (0.285 g, 1.74 mmole) in one lot
  3. stirringThe reaction mixture is stirred 1.5 hours at 65° C.
  4. temperaturecooled to room temperature
  5. concentrationconcentrated in vacuo to a pale oil
  6. customThe oil is chromatographed over 250 g silica gel (230-400 mesh)
  7. washeluting with 20% ethyl acetate/hexane
  8. customafter a 2500 ml forerun collecting 60 ml fractions
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9f17ba78958a400ebc8d620a2c93a641
Source dataset
uspto-grants-1992_05
Patent number
US05116981

Reaction notes

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