Dimethyl Sulfoxide → HCID 15181216, compound

HRID 1087653Notes

Reaction equation

HRID 1087653 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]([N:14]([CH:22]([CH3:24])[CH3:23])[CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][OH:21])([CH3:13])[CH3:12].O>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:22]([N:14]([CH:11]([CH3:13])[CH3:12])[CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH:20]=[O:21])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 15181215HCID 15181215, compound

Product 1

HCID 15181216HCID 15181216, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethyl sulfoxide (25.1 ml, 353 mmol) in CH2Cl2 (75 ml) was added to a stirred solution of oxalyl chloride (14.75 ml, 169 mmol) in CH2Cl2 (370 ml) at -60° C. The reaction mixture was stirred for 1 hour and a propylamino-solution of 6-diisopropylaminohex-4-yn-1-ol (29.07 g, 147.5 mmol) in CH2Cl2 (150 ml) was added and the reaction mixture was stirred for 90 minutes and then allowed to warm to room temperature. Water (200 ml) was then added and the aqueous layer was reextracted with chloroform (3 times 100 ml). The organic layers were combined, washed with brine and dried (MgSO4). Evaporation of the solvent yielded crude product, which was distilled to give 12.96 g of the aldehyde: bp 90-5 (0.25 mm Hg); 1H NMR (CDCl3) δ1.05(d, 12H), 2.00- 2.67(m, 4H), 2.83-3.50(m, 4H), 9.67(s, 1H).

Workup

  1. stirringthe reaction mixture was stirred for 90 minutes
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customEvaporation of the solvent
  5. customyielded crude product, which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-05ed0bed7c304f13aa4312a3fadcb5a8
Source dataset
uspto-grants-1991_07
Patent number
US05036107

Reaction notes

Loading…