Dimethyl Sulfoxide → 4-Ethynylcyclohexane-1-carbaldehyde

HRID 1441037Notes

Reaction equation

HRID 1441037 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15][CH2:14]1)#[CH:12].C(N(CC)CC)C>ClCCl.O>[C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]=[O:20])[CH2:15][CH2:14]1)#[CH:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22421013(trans-4-Ethynylcyclohexyl)methanol

Product 1

HCID 224210104-Ethynylcyclohexane-1-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (354 μl.) was dissolved in dry dichloromethane (3 ml.) at -70° under nitrogen. Dimethyl sulphoxide (650 μl) in dichloromethane (3 ml.) was then added. After stirring for 5 minutes a solution of 4-ethynylcyclohexylmethanol (0.5 g.) in dichloromethane (5 ml.) was added dropwise over 5 minutes. The reaction mixture was stirred for 30 minutes at -70° before triethylamine (2.5 ml.) was added. After warming to 25° over 3 hours, water was added and the organic phase separated, washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine, and dried. Evaporation gave 4-ethynylcyclohexanecarboxaldehyde as a colourless oil.

Workup

  1. additionwas added dropwise over 5 minutes
  2. additionwas added
  3. temperatureAfter warming to 25° over 3 hours
  4. customthe organic phase separated
  5. washwashed with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
  6. customdried
  7. customEvaporation

Sources & evidence

ORD record
ord-552cb557fbf4484a88c43f29a3da85bf
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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