Dimethyl Sulfoxide → HCID 19810541, compound

HRID 373647Notes

Reaction equation

HRID 373647 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([CH:18]([CH2:29][CH2:30][CH2:31][OH:32])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[CH2:11]([CH:18]([CH2:29][CH2:30][CH:31]=[O:32])[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19810564HCID 19810564, compound

Product 1

HCID 19810541HCID 19810541, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of oxalyl chloride (0.9 ml, 10 mmol in 25 ml of CH2Cl2) was slowly added to a flask containing DMSO (1.5 ml, 21 mmol in 3 ml CH2Cl2 at -60° C. under N2. After 5 min, the alcohol from Example 52 (3 g, 10 mmol, 5 ml CH2Cl2) was added dropwise over 5 min period. After stirring the contents for 30 min, Et3N (6.3 ml, 45 mmol) was added and the mixture was warmed to room temperature. The suspension was stirred for 1 h and then poured to a slurry of CH2Cl2 -H2O-ice. The organic layer was washed with dilute HCl, brine, dried over MgSO4, and finally concentrated in vacuo. The crude product was purified by column chromatography (silica gel, Hexane-AcOEt, 4:1) which gave 2.85 g (95%) of the title compound: 1H NMR (CDCl3, 300 MHz) δ: 9.70 (t,J=1Hz,1H,--CHO), 7.40-7.10 (m,10H), 5.05 (s,2H), 3.95 (t,J=6Hz,1H), 2.75 (m,2H), 2.41 (m,2H), and 1.90 (m,2H); DCI-NH3 -MS, m/z 314 (MNH4+, 100%), and 297 (MH+, 20%).

Workup

  1. stirringThe suspension was stirred for 1 h
  2. washThe organic layer was washed with dilute HCl, brine
  3. dry with materialdried over MgSO4
  4. concentrationfinally concentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel, Hexane-AcOEt, 4:1) which

Sources & evidence

ORD record
ord-9d4b2c1d0cac41bb8b967acb46136f4c
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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