Dimethyl Sulfoxide → 3-(Tributylstannyl)prop-2-enal

HRID 1587016Notes

Reaction equation

HRID 1587016 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])/[CH:16]=[CH:17]/[CH2:18][OH:19])[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C>C(Cl)Cl.CCOCC>[CH2:24]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:20][CH2:21][CH2:22][CH3:23])/[CH:16]=[CH:17]/[CH:18]=[O:19])[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10043273(E)-3-(tributylstannyl)prop-2-en-1-ol

Product 1

HCID 109915673-(Tributylstannyl)prop-2-enal

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (17.3 ml) in anhydrous methylene chloride (62 ml) is cooled to -78° C. and dimethylsulfoxide (3.7 ml) is added dropwise. The mixture is stirred for 15 minutes, E-3-tributylstannyl-2-propen-1-ol (10.7 g) in methylene chloride (26 ml) added dropwise, stirred for about 10 minutes, and triethylamine (19.4 ml) added. Stirring is stopped, the mixture allowed to warm to room temperature, then stirred for about 5 minutes, diluted with ether, and washed with water. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography to give the desired product.

Workup

  1. stirringstirred for about 10 minutes
  2. stirringStirring
  3. stirringstirred for about 5 minutes
  4. washwashed with water
  5. dry with materialThe organic solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-9ce71cc17d24431986b04545cd71cfdd
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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