4-(Hydroxymethyl)-1-(phenylsulfonyl)-1H-indol-5-ol → 5-Hydroxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde

HRID 2423127Notes

Reaction equation

HRID 2423127 reaction equation
[OH:1][CH2:2][C:3]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[OH:12][C:11]1[CH:10]=[CH:9][C:8]2[N:7]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 672416334-(Hydroxymethyl)-1-(phenylsulfonyl)-1H-indol-5-ol2×

Product 1

HCID 866217145-Hydroxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehydeYield 45.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(Hydroxymethyl)-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 9, 439 mg, 1.45 mmol) was dissolved in dry DCM (25 mL) and manganese dioxide (0.75 g, 8.7 mmol) was added all in one portion. The reaction mixture was stirred for 2 hours at room temperature and the mixture was filtered through a pad of silica gel. The filtrate was washed with water (1×), dried (MgSO4) and evaporated to give 0.2 g of an orange solid. MS m/z 302 [M+H]+.

Workup

  1. filtrationthe mixture was filtered through a pad of silica gel
  2. washThe filtrate was washed with water (1×)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-eea1c31999ab4cfab4aebdc1df0b6da0
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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