Allyltributylstannane → HCID 70097299, compound

HRID 1978875Notes

Reaction equation

HRID 1978875 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=O)=O.[CH2:26]([Sn](CCCC)(CCCC)CCCC)[CH:27]=[CH2:28].[Cl-].[Li+]>CN(C=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:26]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:27][CH3:28]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 21202059HCID 21202059, compound

Product 1

HCID 70097299HCID 70097299, compoundYield 171.6%

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Argon was passed through a solution of tert-butyl 3-(2-trifluoromethylsulfonyloxy-5-methoxyphenyl)propionate (15 g, 39 mmol), allyltributyl tin (15.8 mL, 51 mmol), and lithium chloride (2.1 g, 51 mmol) in DMF (120 mL) for 10 min, and bis(triphenylphosphine)palladium dchloride (1.5 g, 2.2 mmol) was added. The reaction mixture was heated at 95° C. for 1.5 h and evaporated. The residue was partitioned between 10% KF aquoues solution and ether. The combined extracts were dried and evaporated to give the titled compound (18.5 g).

Workup

  1. customevaporated
  2. customThe residue was partitioned between 10% KF aquoues solution and ether
  3. customThe combined extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-6bbe5fbaf8c74dc089c3c5ae0fc4aeab
Source dataset
uspto-grants-2001_05
Patent number
US06239138B1

Reaction notes

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