Water → 3-(4-Fluorophenyl)-3-methyl-1-tributylstannyl-1-butene

HRID 54259Notes

Reaction equation

HRID 54259 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][CH:10](I)[Sn:11]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:26])([CH3:25])[CH:9]=[CH:10][Sn:11]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 214679673-(4-Fluorophenyl)-3-methyl-1-iodo-1-tributylstannylbutane

Product 1

HCID 676315243-(4-Fluorophenyl)-3-methyl-1-tributylstannyl-1-buteneYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 17.2 grams (0.030 mole ) of 3-(4-fluorophenyl)-3-methyl-1-iodo-1-tributylstannylbutane and 13.7 grams (0.090 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 100 mL of tetrahydrofuran is heated at reflux for about 18 hours. The reaction mixture is cooled and poured into about 500 mL of water. The mixture is then made acidic with aqueous 2N hydrochloric acid and extracted with three 200 mL portions of diethyl ether. The combined extracts are dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel, using 5% methylene chloride in petroleum ether as the eluant. The product-containing fractions are combined and concentrated under reduced pressure, yielding 12.0 grams of 3-(4-fluorophenyl)-3-methyl-1-tributylstannyl-1-butene. The NMR spectrum is consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 18 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionmade acidic with aqueous 2N hydrochloric acid and extracted with three 200 mL portions of diethyl ether
  4. dry with materialThe combined extracts are dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure to a residue
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8160a919727843de88cd84d6a77a8bce
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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