Dimethyl Sulfoxide → 79091-88-6

HRID 1961630Notes

Reaction equation

HRID 1961630 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]([C@@H:15]1[CH2:18][CH2:17][C@H:16]1[CH2:19][OH:20])=[O:14].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][C:13]([C@@H:15]1[CH2:18][CH2:17][C@H:16]1[CH:19]=[O:20])=[O:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1261033574513-00-1

Product 1

HCID 1272133479091-88-6Yield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

At −78° C., oxalyl Chloride (9.2 mL, 106.5 mmol) was solved in dichloromethane (250 mL) and (15.5 mL, 218 mmol) of dimethylsulfoxide in 20 mL of dichloromethane was added. After 15 minutes of stirring at −78° C., Trans-2-Hydroxymethyl-cyclobutanecarboxylic acid methyl ester (14 g, 95.17 mmol) was added in 78 mL of dichloromethane and 10 minutes later triethylamine (67 mL, 479 mmol) was added and the mixture was stirred for 2 h at −78° C. 150 mL of dichloromethane added and 200 mL of water were added and the aqueous phase was extracted with 200 mL of dichlormethane and the combined organic phases were purified with column chromatography on silica using n-heptane/AcOEt (4+1) to yield 11.1 g, (78 mmol, 82% yield) of the title compound as a colourless liquid. MS (m/e): 165.2 (M+Na+)

Workup

  1. customAt −78° C.
  2. additionwas added
  3. stirringthe mixture was stirred for 2 h at −78° C
  4. extractionthe aqueous phase was extracted with 200 mL of dichlormethane
  5. customthe combined organic phases were purified with column chromatography on silica

Sources & evidence

ORD record
ord-0e08f3f471be4f8baa266dc43455543b
Source dataset
uspto-grants-2013_04
Patent number
US08415350B2

Reaction notes

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