Dimethyl Sulfoxide → HCID 86746502, compound

HRID 1464532Notes

Reaction equation

HRID 1464532 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH2:13][C:14]([O:28][CH3:29])([C:21]([CH3:27])=[C:22]([CH3:26])[C:23]=1[O:24][CH3:25])[CH2:15][CH:16]([CH3:20])[CH2:17][CH2:18][OH:19].C(N(CC)CC)C>O.ClCCl>[CH3:11][C:12]1[CH2:13][C:14]([O:28][CH3:29])([C:21]([CH3:27])=[C:22]([CH3:26])[C:23]=1[O:24][CH3:25])[CH2:15][CH:16]([CH3:20])[CH2:17][CH:18]=[O:19]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67823075HCID 67823075, compound

Product 1

HCID 86746502HCID 86746502, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A dichloromethane solution (25 ml) of oxalyl chloride (1 ml, 11 mmole) was cooled to -70° C. under an atmosphere of argon, and a solvent mixture of DMSO (1.7 ml, 22 mmole) and dichloromethane (5 ml) was added dropwise to the solution, while maintaining its temperature at not higher than -60° C. Subsequently, a dichloromethane solution (10 ml) of 3-(3,5,6-trimethyl-1,4-dimethoxybenzyl)-butan-1-ol (3 g, 11 mmole) was added dropwise to the mixed solution, followed by stirring at -70° C. for 15 minutes, and triethylamine (7 ml, 50 mmole) was added dropwise. Then, stirring was continued until the temperature of the reaction solution reached the room temperature, and water (50 ml) was added to the reaction solution, followed by concentration under reduced pressure. The residue was extracted with IPE, and the organic layer was washed with IPE, dried and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give 3-(3,5,6-trimethyl-1,4-dimethoxybenzyl)butanal (2.7 g, 90%).

Workup

  1. additionwas added dropwise to the solution
  2. stirringThen, stirring
  3. additionwas added to the reaction solution
  4. concentrationfollowed by concentration under reduced pressure
  5. extractionThe residue was extracted with IPE
  6. washthe organic layer was washed with IPE
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e26b7fe8b15141b18187883dfb6a0dbc
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

Loading…