Tetrahydrofuran → HCID 67632192, compound

HRID 1441008Notes

Reaction equation

HRID 1441008 reaction equation
[Cl: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.O1CCCC1>O>[Cl: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

4

Reactant 2

HCID 8028TetrahydrofuranHCID 153325683-(4-Chlorophenyl)-3-methyl-1-iodo-1-tributylstannylbutane

Product 1

HCID 67632192HCID 67632192, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 8.7 grams (0.015 mole) of 3-(4-chlorophenyl)-3-methyl-1-iodo-1-tributylstannylbutane and 6.5 mL (0.045 mole) of 1,8-diazabicyclo 5.4.0!undec-7-ene (DBU)in 50 mL of tetrahydrofuran was heated at reflux for about 18 hours. The reaction mixture was cooled and poured into about 225 mL of water. The mixture was then made acidic with aqueous 2N hydrochloric acid and extracted with two 150 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel, using 5% methylene chloride in petroleum ether as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 5.3 grams of 3-(4-chlorophenyl)-3-methyl-1-tributylstannyl-1-butene. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 18 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionmade acidic with aqueous 2N hydrochloric acid and extracted with two 150 mL portions of diethyl ether
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c0833008f0f4f6cbebdecf59a86c337
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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