Dimethyl Sulfoxide → HCID 22421103, compound

HRID 1441054Notes

Reaction equation

HRID 1441054 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([CH:15]1[CH2:20][S:19][C:18]([CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][OH:29])[CH2:24][CH2:23]2)([CH3:21])[S:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.O>[C:11]([CH:15]1[CH2:16][S:17][C:18]([CH:22]2[CH2:23][CH2:24][CH:25]([CH:28]=[O:29])[CH2:26][CH2:27]2)([CH3:21])[S:19][CH2:20]1)([CH3:12])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22421063HCID 22421063, compound

Product 1

HCID 22421103HCID 22421103, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Conditions

Temperature
25 °C

Procedure

Dimethyl sulphoxide (376 μl.) in dichloromethane (2 ml.) was added over 5 minutes to a solution of oxalyl chloride (210 μl.) in dichloromethane (3 ml.) at -70° C. After stirring for a further 5 minutes a solution of 5-t-butyl-2-(4-hydroxymethylcyclohexyl)-2-methyl-1,3-dithiane (650 mg.) in dichloromethane (2 ml.) was added. The reaction mixture was stirred for 30 minutes. Triethylamine (1.5 ml.) was added and the mixture allowed to warm to 25° C. over 3 hours. Water (25 ml.) was added and the crude product obtained by dichloromethane extraction. After washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine and then drying over anhydrous magnesium sulphate the solution was evaporated to give 5-t-butyl-2-(4-formylcyclohexyl)-2- methyl-1,3-dithiane as a gum.

Workup

  1. additionwas added
  2. washAfter washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
  3. dry with materialdrying over anhydrous magnesium sulphate the solution
  4. customwas evaporated

Sources & evidence

ORD record
ord-9cc1b3388f174e7dba6955ce803da217
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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