Dimethyl Sulfoxide → 3-Cyclohexyl-3-formyloxetane

HRID 704155Notes

Reaction equation

HRID 704155 reaction equation
[CH:1]1([C:7]2([CH2:11][OH:12])[CH2:10][O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>ClCCl>[CH:1]1([C:7]2([CH:11]=[O:12])[CH2:8][O:9][CH2:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19373305(3-Cyclohexyloxetan-3-yl)methanol

Product 1

HCID 200755923-Cyclohexyl-3-formyloxetane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3-Cyclohexyl-3-hydroxymethyloxetane (7.0 g) was dissolved in dry dichloromethane (20 ml) and added dropwise to a mixture of oxalyl chloride (1.1 eq, 4 ml) in dry dichloromethane (15 ml). At -70° C. a solution of dimethyl sulphoxide (7.15 ml) in dichloromethane (10 ml) was added. After stirring at -70° C. for 30 minutes triethylamine (29 ml) was added over 30 minutes. The reaction mixture was allowed to warm up to room temperature over a period of 3 hours and then quenched in water. Extraction with dichloromethane, followed by washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine and drying over magnesium sulphate gave a solution which was evaporated to give 3-cyclohexyl-3-formyloxetane as a colourless oil.

Workup

  1. additionwas added over 30 minutes
  2. customquenched in water
  3. extractionExtraction with dichloromethane
  4. washby washing with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
  5. dry with materialdrying over magnesium sulphate
  6. customgave a solution which
  7. customwas evaporated

Sources & evidence

ORD record
ord-e5035303f8c2444db1a1781d07cb5e40
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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