Dimethyl Sulfoxide → 2,3-Dihydro-1-benzofuran-4-carbaldehyde

HRID 1107528Notes

Reaction equation

HRID 1107528 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:20][OH:21])[C:14]=2[CH2:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]1[C:15]2=[CH:16][CH:17]=[CH:18][C:19]([CH:20]=[O:21])=[C:14]2[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18787415(2,3-Dihydro-1-benzofuran-4-yl)methanol

Product 1

HCID 187874492,3-Dihydro-1-benzofuran-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

DMSO (8.10 mL, 114 mmol) was added at -78° C. to a stirred solution of oxalyl chloride in CH2Cl2 (40 mL of a 2M solution). A solution of (2,3-dihydrobenzofuran-4-yl)methanol (8.53 g, 56.9 mmol) in CH2Cl2 (35 mL) was added dropwise, and the solution stirred at -78° C. for 30 min. Triethyl amine (33 mL, 228 mmol) was added cautiously to quench the reaction. The resulting suspension was stirred at room temperature for 30 min and diluted with CH2Cl2 (100 mL). The organic layer was washed three times with water, and twice with brine, and then concentrated in vacuo to an oil (8.42 g, 100%) that was used without purification.

Workup

  1. customto quench
  2. customthe reaction
  3. stirringThe resulting suspension was stirred at room temperature for 30 min
  4. washThe organic layer was washed three times with water
  5. concentrationtwice with brine, and then concentrated in vacuo to an oil (8.42 g, 100%) that
  6. customwas used without purification

Sources & evidence

ORD record
ord-3e8734380d154ec2be50772cf07883dd
Source dataset
uspto-grants-2000_05
Patent number
US06060506

Reaction notes

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