Dimethyl Sulfoxide → 7-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanal

HRID 1584340Notes

Reaction equation

HRID 1584340 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][OH:40])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[O:40])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 212244947-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanol

Product 1

HCID 212244777-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethyl sulfoxide (DMSO) (4 g) in dichloromethane (10 ml) was added dropwise, at temperatures ranging from -60 to -50° C., to a solution of oxalyl chloride [(COCl2)] (2.9 g) in dichloromethane (100 ml). The mixture was stirred for 10 minutes at the same temperature range, to which was then added dropwise a solution of 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanol (4.3 g) in dichloromethane (15 ml). The mixture was stirred for 30 minutes at 0° C., to which was added dropwise at -20° C. triethylamine (10.6 g). The mixture was stirred for further 30 minutes at the same temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:3), was obtained 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)-phenyl]heptanal, which was recrystallized from ethyl acetate-hexane to give colorless prisms, m.p.64-65° C.

Workup

  1. stirringThe mixture was stirred for 30 minutes at 0° C., to which
  2. stirringThe mixture was stirred for further 30 minutes at the same temperature
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationby distilling off the solvent under reduced pressure
  7. washFrom the fraction eluted with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-396bc0b965384a28a3b19ec4081ef19d
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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