Dimethyl Sulfoxide → HCID 23503261, compound

HRID 1835164Notes

Reaction equation

HRID 1835164 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]([C:17]1[O:18][CH:19]=[CH:20][C:21]=1[C:22]([O:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[O:23])[CH2:13][CH:14]([CH3:16])[CH3:15].C(N(CC)CC)C>ClCCl>[CH3:15][CH:14]([CH3:16])[CH2:13][C:12]([C:17]1[O:18][CH:19]=[CH:20][C:21]=1[C:22]([O:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])=[O:23])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23503268HCID 23503268, compound

Product 1

HCID 23503261HCID 23503261, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dimethylsulfoxide (125 μl) was dissolved in dichloromethane (10 ml) and cooled to −78° C. Oxalyl chloride (80 μl) was added dropwise and the mixture was stirred for 15 minutes. Trimethylsilylmethyl 2-(1-hydroxy-3-methylbutyl)furan-3-carboxylate (200 mg) in dichloromethane (10 ml) was added and the mixture was stirred for 20 minutes. Triethylamine (0.49 ml) was added. The mixture was stirred for 20 minutes, and then allowed to warm to ambient temperature. The mixture was poured onto water and then extracted thrice with ethyl acetate. The organic phases were combined, washed with brine, dried, filtered and evaporated to give the sub-title compound (170 mg).

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. stirringThe mixture was stirred for 20 minutes
  3. temperatureto warm to ambient temperature
  4. additionThe mixture was poured onto water
  5. extractionextracted thrice with ethyl acetate
  6. washwashed with brine
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-f73edd07cd404639a164cd6075e3ff73
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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