m-Chloroperbenzoic acid → 3-[(Carbethoxymethyl)sulfinyl]-2-carbethoxyindole

HRID 729005Notes

Reaction equation

HRID 729005 reaction equation
[C:1]([CH2:6][S:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])([O:3][CH2:4][CH3:5])=[O:2].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[C:1]([CH2:6][S:7]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:30])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 150082093-[(Carbethoxymethyl)thio]-2-carbethoxyindole

Product 1

HCID 540892583-[(Carbethoxymethyl)sulfinyl]-2-carbethoxyindole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[(Carbethoxymethyl)thio]-2-carbethoxyindole is treated with m-chloroperbenzoic acid (1 eq.) in methylene chloride at 0° C. The reaction is followed by TLC. After starting material is consumed the reaction mixture is washed with sat. NaHCO3 and sat. NaCl. The organic layer is dried. 3-[(Carbethoxymethyl)sulfinyl]-2-carbethoxyindole may be isolated by flash column chromatography followed by recrystallization.

Workup

  1. customis consumed the reaction mixture
  2. washis washed with sat. NaHCO3 and sat. NaCl
  3. customThe organic layer is dried

Sources & evidence

ORD record
ord-ec486214e05345d89715316f463f0fc7
Source dataset
uspto-grants-1991_09
Patent number
US05051442

Reaction notes

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