Ethanethiol → 4-methyl-1H-indol-5-ol

HRID 603395

Reaction equation

C[O:2][C:3]1[C:4]([CH3:12])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[Cl-].[Cl-].[Cl-].[Al+3].C(S)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:12][C:4]1[C:3]([OH:2])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

Conditions

Temperature: 5 °C

Procedure

5-Methoxy-4-methyl-1H-indole (400.0 mg, 2.48 mmol) was dissolved in CH2Cl2 in an inert atmosphere, and the mixture was cooled to 5° C. Aluminium trichloride (1.65 g, 12.4 mmol) was added, and the reaction mixture was stirred for 5 min, at which point ethanethiol (770.8 mg, 12.4 mmol) was added dropwise. Stirring was continued for 2 h at 5° C. The mixture was poured into ice water (10 mL), stirred for 20 min, and then NaHCO3 was added until a pH>7 was reached. The mixture was extracted with CH2Cl2 (4×), the combined organic phases dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (EtOAc/hexane (v/v) 1:5) to give 133 mg (36%) of the title compound as a white crystalline solid. 1H NMR (400 MHz, CDCl3): 2.46 (s, 3H), 4.40 (br, 1H), 6.49 (s, 1H), 6.76 (d, 1H), 7.10 (d, 1H), 7.19 (s, 1H), 8.03 (br, 1H).

Workup

additionwas added dropwise
stirringstirred for 20 min
extractionThe mixture was extracted with CH2Cl2 (4×)
dry with materialthe combined organic phases dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel flash chromatography (EtOAc/hexane (v/v) 1:5)

Sources & evidence

ORD record: ord-93b4e42a16df4d938d4ab92062c4a523
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Linked notes

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