Tributylstannane → Ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate

HRID 584164Notes

Reaction equation

HRID 584164 reaction equation
[F:1][C:2]([F:18])([CH:8](I)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[F:1][C:2]([F:18])([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 22345534HCID 22345534, compound

Product 1

HCID 15487039Ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoateYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 2,2-difluoro-3-iodo-3-(4-methoxyphenyl)-propionate (5.24 g, 14.2 mmol) in toluene (125 ml) was treated with tributyltin hydride (28.9 g, 0.10 mol) and a few crystals of 2,2′-azobisisobutyronitrile. The resulting solution was then irradiated for 15 minutes at 25° C. with a sun lamp. The solvent was then evaporated in vacuo and the residue was partitioned between acetonitrile and pentane. The acetonitrile fraction was concentrated and chromatographed on silica gel (elution hexane-ethyl acetate, 85:15) to give 2.65 g (76%) of the title material as an oil: bp 90-95° C./0.1 torr (air bath temperature).

Workup

  1. customThe resulting solution was then irradiated for 15 minutes at 25° C. with a sun lamp
  2. customThe solvent was then evaporated in vacuo
  3. customthe residue was partitioned between acetonitrile and pentane
  4. concentrationThe acetonitrile fraction was concentrated
  5. customchromatographed on silica gel (elution hexane-ethyl acetate, 85:15)

Sources & evidence

ORD record
ord-b984792602164982bf84865633fe0722
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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