Dimethyl Sulfoxide → 2-Isobutyl-4-pentenal

HRID 551639Notes

Reaction equation

HRID 551639 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([CH:15]([CH2:18][CH:19]=[CH2:20])[CH2:16][OH:17])[CH:12]([CH3:14])[CH3:13].[Cl-].[NH4+]>C(Cl)Cl.C(N(CC)CC)C>[CH2:11]([CH:15]([CH2:18][CH:19]=[CH2:20])[CH:16]=[O:17])[CH:12]([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 866461312-Isobutylpent-4-en-1-ol

Product 1

HCID 866461322-Isobutyl-4-pentenal

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (5.45 g, 43 mmol) was dissolved in methylene chloride (50 mL), and the solution was cooled to −78° C. Then, dimethyl sulfoxide (6.1 mL) was added dropwise thereto. To the mixture, a methylene chloride (40 mL) solution of 2-isobutylpent-4-en-1-ol (4.9 g, 34 mmol) was subsequently added dropwise, and the mixture was stirred at this temperature for 1 hour. Triethylamine (24 mL) was added thereto, and the mixture was brought to room temperature. A saturated aqueous solution of ammonium chloride was added thereto. The organic layer was separated, washed with water and saturated saline, then dried, and then concentrated to obtain the compound of interest as an oil substance. This compound was used in the next reaction without being purified.

Workup

  1. customwas brought to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and saturated saline
  4. customdried
  5. concentrationconcentrated
  6. customto obtain the compound of interest as an oil substance
  7. customThis compound was used in the next reaction
  8. customwithout being purified

Sources & evidence

ORD record
ord-f188bea5956b45e2a32f39c1ccf6361c
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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