Dimethyl Sulfoxide → HCID 17989257, compound

HRID 1869419Notes

Reaction equation

HRID 1869419 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]([C:14]1[C:15]([O:32][CH3:33])=[C:16]([C:20]([CH3:31])([CH3:30])[CH2:21][C:22]([C:26]([F:29])([F:28])[F:27])([OH:25])[CH2:23][OH:24])[CH:17]=[CH:18][CH:19]=1)([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.O>[OH:25][C:22]([C:26]([F:27])([F:28])[F:29])([CH2:21][C:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH:11]([CH3:13])[CH3:12])[C:15]=1[O:32][CH3:33])([CH3:31])[CH3:30])[CH:23]=[O:24]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 17989141HCID 17989141, compound

Product 1

HCID 17989257HCID 17989257, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

3.17 g (25.04 mmol) of oxalyl chloride is introduced into 83 ml of dichloromethane and cooled to −78° C. At this temperature, 3.9 g (50.08 mmol) of dimethyl sulfoxide, dissolved in 10 ml of dichloromethane, is added in drops. After five minutes of stirring, 7.15 g (21.38 mmol) of 4-(3-isopropyl-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol, dissolved in 21.4 ml of dichloromethane, is added. Then, the reaction mixture is stirred for two hours at this low temperature. 10.8 g (106.9 mmol) of triethylamine is carefully added in drops, and the batch is then stirred vigorously at room temperature for one hour. After water is added and after stirring is done for another ten minutes, it is extracted twice with dichloromethane. The combined organic extracts are washed with 1% sulfuric acid, saturated sodium bicarbonate solution and brine. After drying, and after the solvent is spun off, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). Finally, 5.93 g (83.44%) of the desired aldehyde is obtained.

Workup

  1. additionis added in drops
  2. additionis added
  3. stirringThen, the reaction mixture is stirred for two hours at this low temperature
  4. stirringthe batch is then stirred vigorously at room temperature for one hour
  5. stirringafter stirring
  6. waitis done for another ten minutes
  7. extractionit is extracted twice with dichloromethane
  8. washThe combined organic extracts are washed with 1% sulfuric acid, saturated sodium bicarbonate solution and brine
  9. customAfter drying
  10. customthe residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bc57d63ac01a4c5f9189ccfbec38fe0c
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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