Dimethyl Sulfoxide → HCID 54007205, compound

HRID 2225841Notes

Reaction equation

HRID 2225841 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13](=[O:38])[C:14](=[O:37])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH:25]([OH:36])[C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)=[CH:17][CH:16]=1.CC(C)=O.C(=O)=O>ClCCl.C(N(CC)CC)C>[CH3:11][O:12][C:13](=[O:38])[C:14](=[O:37])[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][CH2:24][C:25]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)=[O:36])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 18522661Acetone cardiceHCID 53844584HCID 53844584, compound

Product 1

HCID 54007205HCID 54007205, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
178 °C

Procedure

A solution of dimethylsulfoxide (0.079 g) in dichloromethane (2 mL) was added over 20 minutes to a stirred solution of oxalyl chloride (0.123 g) in dry dichloromethane (4 mL) maintained throughout at 178° C. by using an acetone-dry ice bath. After 30 minutes at -78° C., a solution of rac-4-[4-hydroxy-4-(2-naphthalenyl)butoxy]-alpha-oxobenzeneacetic acid methyl ester (0.356 g) in dichloromethane (3 mL) was added over 30 minutes and the reaction mixture was stirred for 30 minutes in the acetone-dry ice bath, then triethylamine (0.144 mL) was added. The cooling bath was removed and the reaction was allowed to equilibrate to room temperature, then water was added and the phases were separated. After the aqueous layer was extracted with dichlormethane (2×7 mL), the combined organic layers were washed with brine, then were dried (MgSO4) and evaporated. The residue was purified by flash chromatography over silica gel (ethyl acetate-hexane; 1:3) and then crystallized from ethyl acetate-hexane to furnish in two crops, 0.299 g of 4-[[4-(2-naphthalenyl)-4-oxobutyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 86°-87° C.

Workup

  1. customThe cooling bath was removed
  2. customto equilibrate to room temperature
  3. additionwater was added
  4. customthe phases were separated
  5. extractionAfter the aqueous layer was extracted with dichlormethane (2×7 mL)
  6. washthe combined organic layers were washed with brine
  7. dry with materialwere dried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography over silica gel (ethyl acetate-hexane; 1:3)
  10. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-80a71514ca564dc7b2c04253cc64917e
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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