Dimethyl Sulfoxide → HCID 21469481, compound

HRID 1756966Notes

Reaction equation

HRID 1756966 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH2:20][C:21](=[O:34])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl.O>[C:14]1([CH2:13][C:12](=[O:11])[CH2:20][C:21](=[O:34])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21469489HCID 21469489, compound

Product 1

HCID 21469481HCID 21469481, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-20 °C

Procedure

To a cold (-60° C.), stirred solution of oxalyl chloride (32 mL, 0.37 mol) in dichloromethane (980 mL) was added over 10 minutes a solution of dimethylsulfoxide (52 mL, 0.73 mol) in CH2Cl2 (450 mL). Stirred 2 minutes. To the mixture was added a solution of (±)-2-hydroxy-1-phenyl-4-hexadecanone (105.6 g, 0.3176 mol) in CH2Cl2 (900 mL) over 17 minutes. Stirred 20 minutes. To the mixture was added triethylamine (230 mL, 1.65 mol) over 5 minutes. Stirred 5 minutes. The mixture was allowed to warm to -20° C. and water (1 L) was added. Stirred 30 minutes. The organic layer was washed (1M HCl and saturated NaCl), dried (Na2SO4), and rotoevaporated to an oil. The oil was chromatographed on silica gel using petroleum ether-acetone (45:1) to give a pale yellow oil; yield 67.6 g (64.5%).

Workup

  1. stirringStirred 20 minutes
  2. stirringStirred 5 minutes
  3. stirringStirred 30 minutes
  4. washThe organic layer was washed (1M HCl and saturated NaCl)
  5. dry with materialdried (Na2SO4)
  6. customThe oil was chromatographed on silica gel
  7. customto give a pale yellow oil

Sources & evidence

ORD record
ord-d5d1678903634d7cb0ed62f83d5d9ee6
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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