Dimethyl Sulfoxide → HCID 86624017, compound

HRID 643922Notes

Reaction equation

HRID 643922 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C@@H:18]([CH2:21][CH3:22])[CH2:19][OH:20])=[C:15]([CH:25]=[CH2:26])[CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C@@H:18]([CH2:21][CH3:22])[CH:19]=[O:20])=[C:15]([CH:25]=[CH2:26])[CH:14]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66751010HCID 66751010, compound

Product 1

HCID 86624017HCID 86624017, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

DMSO (4.9 mL, 68.8 mml) is added to a solution of oxalyl chloride (4.5 mL, 51.6 mmol) in dry DCM (100 mL) at −78° C. and the mixture is stirred at −78° C. for 10 min. A solution of (R)-2-(4-methoxy-2-vinylbenzyl)-butan-1-ol (5.70, 25.9 mmol) in DCM (30 mL) is added. The mixture is stirred at −78° C. for 15 min and then at −40˜−30° C. for 1 h. Triethylamine (18 mL, 129 mmol) is added slowly. The mixture is stirred at −10˜0° C. for 15 min. The mixture is partitioned between DCM and aq. NH4Cl. The organic extract is dried with MgSO4 and concentrated to give the title compound as an orange oil.

Workup

  1. stirringThe mixture is stirred at −78° C. for 15 min
  2. waitat −40˜−30° C. for 1 h
  3. stirringThe mixture is stirred at −10˜0° C. for 15 min
  4. customThe mixture is partitioned between DCM and aq. NH4Cl
  5. extractionThe organic extract
  6. dry with materialis dried with MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8948d888a9294fbea0bc0fac8aca1667
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

Loading…