Ethanethiol → Methyl 3-[5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

HRID 327242Notes

Reaction equation

HRID 327242 reaction equation
C(S[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15]C)[CH:13]=2)[NH:8][C:7]=1[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])(C)(C)C.[Al+3].[Cl-].[Cl-].[Cl-].CCS.C(C(C(C([O-])=O)O)O)([O-])=O>C(Cl)Cl>[OH:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:6]2

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 38061142,3-DihydroxybutanedioateHCID 6451240Aluminum(III) ChlorideHCID 14980549Methyl 3-{5-methoxy-3-[(2-methyl-2-propanyl)sulfanyl]-1H-indol-2-yl}-2,2-dimethylpropanoate

Product 1

HCID 18947616Methyl 3-[5-hydroxyindol-2-yl]-2,2-dimethylpropanoateYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound from step A (25.50 g, 73 mmol) in CH2Cl2 (250 ml) at 0° C. was added AlCl3 (87.70 g, 9 mol eq.) portion-wise. When the addition was complete, the ice-bath was removed and the mixture was stirred at RT for 3 hours. EtSH (27 ml, 5 mol eq.) was added and the resulting mixture was stirred for a further 5 hours. It was then slowly poured onto an ice-cold 1M solution of Na, K tartrate. The product was extracted into CH2Cl2 (×2) and the organic phase was washed with aq. NaCl (×3). Conventional work-up followed chromatography on silica gel using EtOAc/hexane 1:5 to 3:2 afforded 13.60 g of-the title compound, 75% yield.

Workup

  1. additionWhen the addition
  2. customthe ice-bath was removed
  3. stirringthe resulting mixture was stirred for a further 5 hours
  4. extractionThe product was extracted into CH2Cl2 (×2)
  5. washthe organic phase was washed with aq. NaCl (×3)

Sources & evidence

ORD record
ord-a6eed0afa1544d9798c333be9599e94e
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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