Dimethyl Sulfoxide → HCID 10535409, compound

HRID 1830534Notes

Reaction equation

HRID 1830534 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[N:13]=[C:14]([CH2:21][OH:22])[CH:15]=[C:16]2[CH:20]=[CH:19][O:18][C:17]=12.C(=O)=O.CC(C)=O>C(Cl)Cl>[Cl:11][C:12]1[N:13]=[C:14]([CH:21]=[O:22])[CH:15]=[C:16]2[CH:20]=[CH:19][O:18][C:17]=12

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 105116877-Chlorofuro[2,3-c]pyridine-5-methanolHCID 18522661Acetone cardice2×

Product 1

HCID 10535409HCID 10535409, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (3.1 mL, 35 mmol) is dissolved in 200 mL CH2Cl2 in dried flask under N2. The flask is placed in a dry-ice/acetone bath at −78° C., DMSO (4.95 mL, 70 mmol) in 10 mL CH2Cl2 is added drop-wise, and the mixture is stirred for 20 min. C4 (5.5 g, 30 mmol) in 10 mL CH2Cl2 is added, and the reaction is stirred 30 min at −78° C. TEA (21.3 mL, 153 mmol) is then added. The reaction is stirred 30 min in the dry-ice/acetone bath at −78° C., an ice bath replaced the dry-ice/acetone bath, and the reaction is stirred 1 h and is washed with 100 mL 1:1 saturated NaCl/NaHCO3. The organic layer is dried over anhydrous K2CO3, filtered, and then concentrated in vacuo to afford 7-chlorofuro[2,3-c]pyridine-5-carbaldehyde (C6) as a pale yellow solid (97% yield). MS (EI) for C8H4ClNO2 m/z: 181 (M)+.

Workup

  1. customThe flask is placed in a dry-ice/acetone bath at −78° C.
  2. stirringthe reaction is stirred 30 min at −78° C
  3. customan ice bath replaced
  4. washis washed with 100 mL 1:1 saturated NaCl/NaHCO3
  5. dry with materialThe organic layer is dried over anhydrous K2CO3
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-324eb493b729440d9251f9a4205a10d5
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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