Dimethyl Sulfoxide → HCID 14986674, compound

HRID 1494110Notes

Reaction equation

HRID 1494110 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]([CH3:34])([CH2:17][CH:18]([CH2:31][CH2:32][OH:33])[CH2:19][CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]([CH3:34])([CH2:17][CH:18]([CH2:31][CH:32]=[O:33])[CH2:19][CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:26])[CH3:25])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14986673Methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate

Product 1

HCID 14986674HCID 14986674, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3.4 mL (48 mmol) dimethyl sulfoxide in 140 mL dry methylene chloride at -78° C. is added dropwise 3.0 mL (35 mmol) oxalyl chloride. The solution is stirred for 15 minutes and a solution of 2.57 g (7.1 mmol) methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate in 20 mL dry methylene chloride is added slowly. The solution is stirred at -60° C. for 15 minutes and 15 mL (0.11 mole) triethylamine is added. The reaction is allowed to warm to room temperature and diluted with methylene chloride. The organic layer is washed with saturated aqueous sodium bicarbonate solution, water and brine. The organic phase is dried, filtered and concentrated to dryness. The oil is dissolved in ether and the solution is washed with water. The organic phase is dried, filtered and concentrated to give methyl 2,2-dimethyl-4-formylmethyl-8-(t-butyldimethylsiloxy)-octanoate; NMR (CDCl3) delta 9.8 (t,1H), 3.67 (s,3H), 1.2 (s,6H), 0.89 (s,9H).

Workup

  1. stirringThe solution is stirred at -60° C. for 15 minutes
  2. washThe organic layer is washed with saturated aqueous sodium bicarbonate solution, water and brine
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionThe oil is dissolved in ether
  7. washthe solution is washed with water
  8. customThe organic phase is dried
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-64eea7e9683e44d1999c9c47dda55ea3
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

Loading…