Water → 3-Formyl-3-n-propyloxetane

HRID 2165867Notes

Reaction equation

HRID 2165867 reaction equation
C(Cl)(=O)C(Cl)=O.[OH:7][CH2:8][C:9]1([CH2:13][CH2:14][CH3:15])[CH2:12][O:11][CH2:10]1.C(N(CC)CC)C.O>ClCCl>[CH:8]([C:9]1([CH2:13][CH2:14][CH3:15])[CH2:12][O:11][CH2:10]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1838902-Propyl-2-oxetanemethanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution on dimethyl sulphoxide (12 ml) in dry dichloromethane (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-propyloxetane (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 further extracted with fresh 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) 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 further extracted with fresh 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-3dd4a68a9ce74b5eb36cd87ae2e702a8
Source dataset
uspto-grants-1990_07
Patent number
US04942173

Reaction notes

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