Water → HCID 66671882, compound

HRID 1261539Notes

Reaction equation

HRID 1261539 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:32][CH:31]=3)[CH:19]=[CH:20][C:21]=2OS(C(F)(F)F)(=O)=O)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[Li+].[Cl-].[CH2:43]([Sn](CCCC)(CCCC)CCCC)[CH:44]=C.O>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:32][CH:31]=3)[CH:19]=[CH:20][C:21]=2[CH:43]=[CH2:44])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 86617901HCID 86617901, compound

Product 1

HCID 66671882HCID 66671882, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

g of ethyl 3″-tert-butyl-4″-diethylamino-4′-trifluoromethanesulfonyloxy[1,1′;3′,1″]terphenyl-4-carboxylate (2 mmol) are dissolved at room temperature in 23 mL of dimethylformamide, and 250 mg of LiCl (6 mmol) and 0.74 mL of allyltributyltin (2.4 mmol) are then added. The reaction medium is heated and, at 40° C., 70 mg of dichlorobis(triphenylphosphine)palladium (0.1 mmol) are added and the reaction medium brought to 120° C. and stirred for 20 minutes. The reaction is stopped by adding 30 mL of water and then extracted with 30 mL of ethyl acetate. The organic phases are washed with 80 mL of water and then dried over magnesium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on silica gel (eluent: heptane). 940 mg of ethyl 3″-tert-butyl-4″-diethylamino-4′-vinyl[1,1′;3′,1″]terphenyl-4-carboxylate are obtained (yield=100%).

Workup

  1. custombrought to 120° C.
  2. extractionextracted with 30 mL of ethyl acetate
  3. washThe organic phases are washed with 80 mL of water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvents are evaporated off
  6. customthe residue is then purified by chromatography on silica gel (eluent: heptane)

Sources & evidence

ORD record
ord-eebbba7c7f8240d7ab07a2055aafbbaa
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

Loading…