Dimethyl Sulfoxide → HCID 59776397, compound

HRID 1008766Notes

Reaction equation

HRID 1008766 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([CH3:25])([CH2:15][C:16]#[C:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH2:13][OH:14].O>C(Cl)Cl>[CH3:11][C:12]([CH3:25])([CH2:15][C:16]#[C:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 59776372HCID 59776372, compound

Product 1

HCID 59776397HCID 59776397, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (152 μl; 1.74 mmol) in DCM (4 mL) at −78° C. was added a solution of DMSO (237 μl; 3.34 mmol) in DCM (2 mL). The mixture was stirred for 5 min before the addition of a solution of 2,2-dimethyl-6-morpholin-4-ylhex-4-yn-1-ol (307 mg; 1.45 mmol) in DCM (2 mL). The mixture was stirred again at −78° C. for 15 min and TEA (1.05 mL) was added. It was then brought back to rt and stirred for 2 h. Water was added. Organic phase was washed with a saturated solution of NaHCO3 and brine. It was dried over magnesium sulfate, filtrated and concentrated to give the title compound as a colorless oil (303 mg, quantitative). 1H NMR (CDCl3) δ: 9.51 (s, 1H), 3.73 (m, 4H), 3.27 (m, 2H), 2.56 (m, 4H), 2.36 (m, 2H), 1.14 (s, 6H).

Workup

  1. customwas then brought back to rt
  2. stirringstirred for 2 h
  3. washOrganic phase was washed with a saturated solution of NaHCO3 and brine
  4. dry with materialIt was dried over magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8998c307d8c74dfdafca19fd140dcfa3
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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