Tributylstannane → HCID 14182040, compound

HRID 483747Notes

Reaction equation

HRID 483747 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3](Cl)([C:20]1[CH:25]=[C:24]([F:26])[C:23]([O:27][CH2:28][CH3:29])=[C:22]([F:30])[CH:21]=1)[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[F:32][C:2]([F:1])([F:33])[CH:3]([C:20]1[CH:21]=[C:22]([F:30])[C:23]([O:27][CH2:28][CH3:29])=[C:24]([F:26])[CH:25]=1)[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 14182039HCID 14182039, compound

Product 1

HCID 14182040HCID 14182040, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

(RS)-1,1,1-Trifluoro-2-chloro-2-(3,5-difluoro-4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane (0.2 g), α,α'-azoisobutyronitrile (0.01 g) and tri-n-butyltin hydride (0.13 g) were mixed in toluene (10 cm3), and the reaction mixture heated at 95° C. for 8 hours. Analysis by gas liquid chromatography then showed no starting material remaining. The solvent was evaporated under reduced pressure, and the residual oil purified by chromatography on a silica gel support, eluting with n-hexane contaning 5% by volume ethyl acetate, to give 1,1,1-trifluoro-2-(3,5-difluoro-4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)-propane (0.14 g) as a colourless oil (97% pure).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residual oil purified by chromatography on a silica gel support
  3. washeluting with n-hexane contaning 5% by volume ethyl acetate

Sources & evidence

ORD record
ord-2869fbd08c704f06a9c4907d68f8bbac
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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