Dimethyl Sulfoxide → HCID 15132295, compound

HRID 2050642Notes

Reaction equation

HRID 2050642 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]([C:25]1[CH:26]=[C:27]([Si:30]([CH3:33])([CH3:32])[CH3:31])[O:28][CH:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)CC)C>ClCCl>[O:11]=[C:12]([C:25]1[CH:26]=[C:27]([Si:30]([CH3:33])([CH3:32])[CH3:31])[O:28][CH:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuran2×

Product 1

HCID 15132295HCID 15132295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of dimethyl sulfoxide (0.5 ml) and dichloromethane (5 ml) was added dropwise to a solution of oxalyl chloride (0.36 ml, 4.18 mmol) in dichloromethane (5 ml) at -78° under argon. After 5 minutes, a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (Compound 25, 1.01 g, 2.98 mmol) in dichloromethane (5 ml), followed by triethylamine (1.66 ml, 11.9 mmol) after 20 minutes, was added. Stirring was continued for 3 hours while the cooling bath attained room temperature. The mixture was quenched with water and extracted with dichloromethane. The dried (magnesium sulfate) extracts on evaporation gave a residue which was purified by a silica column using 2.5% ethyl ether/hexane. Fractions with Rf of about 0.27 (5% ethyl ether/hexane) on evaporation gave the titled ketone as an off-white solid.

Workup

  1. additionwas added
  2. waitwas continued for 3 hours while the cooling bath attained room temperature
  3. customThe mixture was quenched with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe dried (magnesium sulfate)
  6. customextracts on evaporation
  7. customgave a residue which
  8. customwas purified by a silica column
  9. customFractions with Rf of about 0.27 (5% ethyl ether/hexane) on evaporation

Sources & evidence

ORD record
ord-e919aa0167854b94af9ad4a9e1f26cf1
Source dataset
uspto-grants-1991_05
Patent number
US05013850

Reaction notes

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