Methanol → HCID 54146950, compound

HRID 1452394Notes

Reaction equation

HRID 1452394 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][S:2]1.CO.[C:13]([C:15]1C(=O)C(Cl)=C(Cl)[C:17](=O)[C:16]=1C#N)#N.O>C(Cl)Cl>[CH2:1]1[C:10]2[CH:9]=[C:8]3[C:7](=[CH:6][C:5]=2[CH:4]=[CH:3][S:2]1)[CH:17]=[CH:16][CH:15]=[CH:13]3

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 78149Isothiochroman

Product 1

HCID 54146950HCID 54146950, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The thioisochroman from step 1 (Example 13) (100.0 mg,0.40 mmmol) was dissolved in CH2Cl2 (12 ml) and MeOH (4 ml) followed by the addition of DDQ (109.0 mg,0.48 mmol,1.2 eq [2]) at R.T. The resulting mixture was stirred at room temperature overnight. H2O was added and it was extracted with CH2Cl2. The combined organic phases were washed with water, dried over MgSO4, filtered and concentrated in vacuum. The crude obtained was flash chromatographed using toluene:ethylacetate (95:5) to give the trans titled compound (65.0 mg,0.23 mmol) in 58% yield (MP: 84° C.).

Workup

  1. extractionit was extracted with CH2Cl2
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe crude obtained
  7. customchromatographed

Sources & evidence

ORD record
ord-66f0d77329894bdbaab2172597c24db7
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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