HCID 14210385, compound → HCID 14210386, compound

HRID 1030211Notes

Reaction equation

HRID 1030211 reaction equation
[CH3:1][C:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1)([CH3:5])[C:3]#[CH:4]>ClC1C=CC=CC=1Cl>[CH3:5][C:2]1([CH3:1])[CH:3]=[CH:4][C:8]2[CH:9]=[C:10]([S:13]([CH3:16])(=[O:14])=[O:15])[CH:11]=[CH:12][C:7]=2[O:6]1

Participants

3

Reactant 1

HCID 14210385HCID 14210385, compound

Product 1

HCID 14210386HCID 14210386, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
200 °C

Procedure

To 1,2-dichlorobenzene (230 ml) at 200° C. was added 3-methyl-3-(4-mesylphenoxy)-1-butyne (130 g) dropwise over a period of 1.5 hours. The reaction mixture was stirred at 200° C. for an additional 2 hours followed by removal of 1,2-dichlorobenzene by distillation under reduced pressure. The residue was dissolved in diisopropyl ether (100 ml) and treated with activated carbon. The mixture was filtered and the filtrate afforded the precipitate, which was collected, washed with diisopropyl ether, and dried to give 2,2-dimethyl-6-mesyl-2H-1-benzopyran (77 g).

Workup

  1. customfollowed by removal of 1,2-dichlorobenzene by distillation under reduced pressure
  2. dissolutionThe residue was dissolved in diisopropyl ether (100 ml)
  3. additiontreated with activated carbon
  4. filtrationThe mixture was filtered
  5. customthe filtrate afforded the precipitate, which
  6. customwas collected
  7. washwashed with diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-97eaeb4656f44d4f99dd219f0acd37e0
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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