HCID 90070457, compound → HCID 90070459, compound

HRID 590519Notes

Reaction equation

HRID 590519 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([OH:12])[CH2:4]1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[OH:1][CH2:2][CH:3]1[CH2:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5](=[O:12])[CH2:4]1

Participants

4

Reactant 1

HCID 90070457HCID 90070457, compound

Product 1

HCID 90070459HCID 90070459, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-(Hydroxymethyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-4-ol (1.2 g, 6.7 mmol) was dissolved in 1,4-dioxane (30 mL) and manganese dioxide (5.8 g, 67 mmol) was added portion-wise at room temperature. The mixture was stirred for 1 h 40 min. The solution was filtered through celite, washed with 1,4-dioxane and concentrated in vacuo. The crude residue was purified on silica gel using a gradient elution of 40-60% ethyl acetate in 40-60 petroleum ether to yield the title compound as a yellow oil (0.745 g, 62%).

Workup

  1. filtrationThe solution was filtered through celite
  2. washwashed with 1,4-dioxane
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified on silica gel using
  5. washa gradient elution of 40-60% ethyl acetate in 40-60 petroleum ether

Sources & evidence

ORD record
ord-b142ee672ffb4a2cbfe5bfe9d129f5eb
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Reaction notes

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