Dimethyl Sulfoxide → HCID 20211025, compound

HRID 1906899Notes

Reaction equation

HRID 1906899 reaction equation
C(Cl)(=O)C(Cl)=O.ClCCl.CS(C)=O.[CH3:14][C:15]1[C:20]2[CH2:21][CH2:22][CH:23]([CH2:25][OH:26])[O:24][C:19]=2[CH:18]=[C:17]([CH3:27])[CH:16]=1>O.C(N(CC)CC)C>[CH3:14][C:15]1[C:20]2[CH2:21][CH2:22][CH:23]([CH:25]=[O:26])[O:24][C:19]=2[CH:18]=[C:17]([CH3:27])[CH:16]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 20211036HCID 20211036, compound

Product 1

HCID 20211025HCID 20211025, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 72 parts of ethanedioyl dichloride in 650 parts of dichloromethane were added, during a period of 10 minutes, 83.5 parts of dimethyl sulfoxide at -60° C. and under nitrogen atmosphere. After stirring for 10 minutes, a solution of 97 parts of 3,4-dihydro-5,7-dimethyl-2H-1-benzopyran-2-methanol in 130 parts of dichloromethane was added during a 5 minutes period. The whole was stirred for 15 minutes and 242.9 parts of N,N-diethylethanamine were added. The reaction mixture was allowed to reach room temperature. It was poured into water. The product was extracted with dichloromethane. The extract was washed successively with water, a hydrochloric acid solution 10%, water, a sodium hydrogen carbonate solution 10% and water, dried, filtered and evaporated. The oily residue was crystallized from a small amount of petroleumether. The product was filtered off and dried, yielding 58 parts (72%) of 3,4-dihydro-5,7-dimethyl-2H-1-benzopyran-2-carboxaldehyde (intermediate 34).

Workup

  1. customat -60° C.
  2. stirringThe whole was stirred for 15 minutes
  3. customto reach room temperature
  4. extractionThe product was extracted with dichloromethane
  5. washThe extract was washed successively with water
  6. dry with materiala hydrochloric acid solution 10%, water, a sodium hydrogen carbonate solution 10% and water, dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue was crystallized from a small amount of petroleumether
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-0dad1539949a443a8072420c35737e70
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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