Dimethyl Sulfoxide → 2,3,4,5-Tetrahydro-1-benzoxepin-6-carboxaldehyde

HRID 342082Notes

Reaction equation

HRID 342082 reaction equation
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.[O:11]1[C:17]2[CH:18]=[CH:19][CH:20]=C[C:16]=2[CH2:15][CH:14](CO)[CH2:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]1[C:17]2=[CH:18][CH:19]=[CH:20][C:6]([CH:5]=[O:9])=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18787485HCID 18787485, compound

Product 1

HCID 187873792,3,4,5-Tetrahydro-1-benzoxepin-6-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

DMSO (1.85 ml, 26 mmol) was added slowly to a -78° C. solution of oxalyl chloride in methylene chloride (10 ml of 2M, 20 mmol). To this solution was added slowly a solution of 2,3,4,5-tetrahydrobenzoxepin-4-methanol (2.3 g, 13 mmol) in methylene chloride, and the mixture was stirred 30 min at -78° C. Triethyl amine (7.53 ml, 52 mmol) was added slowly to the reaction mixture, which was then allowed to warm to room temperature. The mixture was diluted with methylene chloride (50 ml) and washed with water and then brine. The organic layer was concentrated in vacuo to an oil (2.28 g, 100%).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. concentrationThe organic layer was concentrated in vacuo to an oil (2.28 g, 100%)

Sources & evidence

ORD record
ord-568d8fab32a94863b58c8e14890a3325
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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