Dimethylformamide → HCID 19801174, compound

HRID 1646601Notes

Reaction equation

HRID 1646601 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[CH2:12]([Sn](CCCC)(CCCC)CC=C)[CH2:13][CH2:14]C.CN(C)C=O.[F-].[K+]>C(N(CC)CC)C>[CH2:14]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])[CH:13]=[CH2:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 90628AllyltributylstannaneHCID 987131-Indanone, 4-bromo-HCID 522689Potassium Fluoride

Product 1

HCID 19801174HCID 19801174, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

15 g of 4-bromo-1-indanone, 24 ml of tributyl allyl stannane, 150 ml of dimethylformamide, 0.82 g of tetrakis triphenyl phosphine palladium and 7.89 g of triethylamine are taken to 120° C. for one hour. After cooling to 20° C., the reaction mixture is poured over 300 ml of an aqueous solution of potassium fluoride, agitated, and filtered on celite; the filtrate is extracted with isopropyl ether. The insoluble part is taken up with ethyl acetate and filtered on celite. The reunited organic phases are washed with water saturated with sodium chloride, dried and brought to dryness under reduced pressure. The residue is chromatographed on silica with hexane-ethyl acetate (9-1) and 11.84 g of expected product is recovered.

Workup

  1. filtrationfiltered on celite
  2. extractionthe filtrate is extracted with isopropyl ether
  3. filtrationfiltered on celite
  4. washThe reunited organic phases are washed with water saturated with sodium chloride
  5. customdried
  6. customThe residue is chromatographed on silica with hexane-ethyl acetate (9-1) and 11.84 g of expected product
  7. customis recovered

Sources & evidence

ORD record
ord-191d19c4de6d4199a14fc5cde4f2f0ef
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

Loading…