Dimethyl Sulfoxide → HCID 178442346, compound

HRID 1198841Notes

Reaction equation

HRID 1198841 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C@H:29]3[CH2:34][CH2:33][C@H:32]([CH2:35][OH:36])[CH2:31][CH2:30]3)=[CH:25][CH:24]=2)=[N:21][CH:22]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C@H:29]3[CH2:30][CH2:31][C@H:32]([CH:35]=[O:36])[CH2:33][CH2:34]3)=[CH:25][CH:24]=2)=[N:21][CH:22]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178442347HCID 178442347, compound

Product 1

HCID 178442346HCID 178442346, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A solution of 0.94 ml of oxalyl chloride in 25 ml of dry methylene chloride is treated dropwise at -60° C. within 10 minutes with a solution of 1.56 ml of dimethyl sulphoxide in 5 ml of methylene chloride. 2 minutes later the reaction mixture is treated dropwise at -60° C. within 10 minutes with a solution of 3.51 g of 5-hexyl-2-[p-(trans-4-(hydroxymethyl)cyclohexyl)phenyl]pyridine in 10 ml of methylene chloride and stirred at -60° C. for a further 15 minutes. Thereafter, the reaction mixture is treated with 7 ml of triethylamine, left to warm to room temperature and then poured into water and extracted with methylene chloride. The organic phase is washed twice with water, dried over magnesium sulphate and evaporated. The 5-hexyl-2-[p-(trans- -4-formylcyclohexyl)phenyl]pyridine obtained is purified by chromatography on silica gel.

Workup

  1. waitleft
  2. temperatureto warm to room temperature
  3. extractionextracted with methylene chloride
  4. washThe organic phase is washed twice with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-b1bd2313698e44508d80c066bf588e8e
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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