Dimethyl Sulfoxide → HCID 19351600, compound

HRID 581732Notes

Reaction equation

HRID 581732 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[C:21]([F:22])=[CH:20][C:16]2[S:17][CH:18]=[CH:19][C:15]=2[C:14]=1[F:23].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C.O>[F:23][C:14]1[C:15]2[CH:19]=[CH:18][S:17][C:16]=2[CH:20]=[C:21]([F:22])[C:13]=1[CH:12]=[O:11]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18691590HCID 18691590, compound

Product 1

HCID 19351600HCID 19351600, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.22 ml of oxalyl chloride in 10 ml of methylene chloride is added 0.35 ml of dimethyl sulfoxide at -78° C. Then, to the resulting solution is added dropwise a solution of 0.20 g of 5-hydroxymethyl-4,6-difluorobenzo[b]thiophene in 3 ml of methylene chloride. At the same temperature, the resulting mixture is stirred for one hour, and then, 0.70 ml of triethylamine is added thereto. The temperature of the resulting mixture is elevated to room temperature, and thereafter, 10 ml of water and 10 ml of ethyl acetate are added thereto, after which the resulting organic layer is separated, washed successively with water and a saturated saline solution and then dried over anhydrous magnesium sulfate. Then, the solvent is removed from the thus dried layer by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluent:hexane], to obtain 0.20 g of colorless, solid 4,6-difluorobenzo[b]thiophene-5-carbaldehyde.

Workup

  1. customis elevated to room temperature
  2. customafter which the resulting organic layer is separated
  3. washwashed successively with water
  4. dry with materiala saturated saline solution and then dried over anhydrous magnesium sulfate
  5. customThen, the solvent is removed from the thus dried layer by distillation under reduced pressure
  6. customThe residue obtained
  7. customis purified by a column chromatography [eluent:hexane]

Sources & evidence

ORD record
ord-8fcea7ecb2a14cd7a3c990dbfba16722
Source dataset
uspto-grants-1999_07
Patent number
US05922721

Reaction notes

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