Dimethyl Sulfoxide → 3-Formyl-3-n-propyloxetane

HRID 1197316Notes

Reaction equation

HRID 1197316 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1([CH2:17][CH2:18][CH3:19])[CH2:16][O:15][CH2:14]1.C(N(CC)CC)C>ClC(Cl)Cl.ClCCl.O>[CH:12]([C:13]1([CH2:17][CH2:18][CH3:19])[CH2:16][O:15][CH2:14]1)=[O:11]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1838902-Propyl-2-oxetanemethanol

Product 1

HCID 150219983-Formyl-3-n-propyloxetaneYield 106.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethyl sulphoxide (12 ml) in dry trichloromethane (4.0 ml) was added to a solution of oxalyl chloride (7.4 ml) in dichloromethane (25 ml) stirred at -70° under nitrogen. After the addition was complete the resulting mixture was stirred for a further 5 minutes at -70° before a solution of 3-hydroxymethyl-3-n-propyl oxetane (10.0 g) in dichloromethane (25 ml) was added, dropwise, over 10 minutes. The resulting mixture was allowed to stir for a further 30 minutes when neat triethylamine (54 ml) was added over approximately 30 minutes. The reaction mixture was allowed to warm to room temperature over 3 hours when it was poured into water. The organic phase was separated and the aqueous layer was further extracted with dichloromethane. The combined organic extracts were washed with dilute hydrochloric acid, saturated sodium bicarbonate and brine. The resulting organic phase was dried over anhydrous magnesium sulphate and evaporated in vacuo to give 3-formyl-3-n-propyloxetane (10.5 g) (European Patent Application No. 216624) as a yellow oil.

Workup

  1. additionAfter the addition
  2. additionwas added
  3. additionwas added over approximately 30 minutes
  4. customThe organic phase was separated
  5. extractionthe aqueous layer was further extracted with dichloromethane
  6. washThe combined organic extracts were washed with dilute hydrochloric acid, saturated sodium bicarbonate and brine
  7. dry with materialThe resulting organic phase was dried over anhydrous magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-8cece6389edd49799adfd085f618d78b
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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