Ethanethiol → Methyl 3-[N-methyl-6-hydroxyindol-2-yl]-2,2-dimethylpropanoate

HRID 327237Notes

Reaction equation

HRID 327237 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11]C)[CH:9]=2)[C:4](SC(C)(C)C)=[C:3]1[CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21].C(S)C.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH:4]=[C:3]1[CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18947604Methyl 3-[N-methyl-3-(t-butylthio)-6-methoxyindol-2-yl]-2,2-dimethylpropanoate

Product 1

HCID 18947623Methyl 3-[N-methyl-6-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution of 940 mg of the indole ester from Step B and 1.6 mL of ethanethiol in CH2Cl2 (50 mL) was added portion-wise 4.3 g of AlCl3. After complete addition, the mixture was stirred at R.T. for 2 h. The mixture was then cooled to 0 ° C. and carefully quenched with a solution of 0.5M Na,K tartrate (200 mL) and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and evaporated to dryness to give a solid which was chromatographed on flash silica gel using ethyl acetate:hexane (30:70) as eluant to afford the title compound; m.p. 125°-126° C.

Workup

  1. additionAfter complete addition
  2. temperatureThe mixture was then cooled to 0 ° C.
  3. customcarefully quenched with a solution of 0.5M Na,K tartrate (200 mL)
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated to dryness
  7. customto give a solid which
  8. customwas chromatographed on flash silica gel

Sources & evidence

ORD record
ord-5ad4c0d20ab6439193cbb478431b7395
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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