Methanol → HCID 54146950, compound

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Reaction Steps

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.).

Provenance & Evidence