Dimethyl Sulfoxide → HCID 22375156, compound

HRID 1956092Notes

Reaction equation

HRID 1956092 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([CH:14]1[CH2:19][CH2:18][CH:17]([CH:20]2[CH2:25][CH2:24][CH:23]([O:26][CH2:27][CH2:28][CH2:29][OH:30])[CH2:22][CH2:21]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13].[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[CH2:11]([CH:14]1[CH2:19][CH2:18][CH:17]([CH:20]2[CH2:25][CH2:24][CH:23]([O:26][CH2:27][CH2:28][CH:29]=[O:30])[CH2:22][CH2:21]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 22375168HCID 22375168, compound

Product 1

HCID 22375156HCID 22375156, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

DMSO in an amount of 2.13 ml (0.03 mol) was added dropwise to a mixture of 1.74 ml (0.02 mol) of oxalic acid chloride and 40 ml of dichloromethane at -50° C. and stirred for 10 min. While keeping inside of the reaction system at -60°C., this solution was added dropwise with a solution of 2.82 g (0.01 mol) of the 4-(4-propylcyclohexyl)-(3-hydroxypropyloxy)cyclohexane obtained in the second stage and dissolved in 20 ml of dichloromethane and stirred for 1 hour. To this solution was added 14 ml of triethylamine, temperature of the solution was returned to a room temperature, stirred for 15 min, and the solution was added with 80 ml of an aqueous solution saturated with ammonium chloride. The organic layer was separated and dried over anhydrous magnesium sulfate. After the magnesium sulfate was separated, the solvent was distilled off under a reduced pressure, and the residue was subjected to a silica gel column chromatography (eluate: toluene/ethylacetate (9/1)) to obtain 1.93 g of a crude 4-(4-propylcyclohexyl)-(3-oxopropyoxy) cyclohexane. This product was recrystallized from 12 ml of ethanol to obtain 1.3 g (yield 46%) of 4-(4-propylcyclohexyl)-(3-oxopropyloxy)cyclohexane.

Workup

  1. customWhile keeping inside of the reaction system at -60°C.
  2. customobtained in the second stage
  3. stirringstirred for 1 hour
  4. customwas returned to a room temperature
  5. stirringstirred for 15 min
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter the magnesium sulfate was separated
  9. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-c3afa2b6700d4792b9217ac5847bd2de
Source dataset
uspto-grants-1998_07
Patent number
US05779936

Reaction notes

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