Potassium Carbonate → t-butyl 2-(2-(2-oxo-2-(1-pentyl-1H-indol-3-yl)ethyl)phenoxy)acetate

HRID 61308Notes

Reaction equation

HRID 61308 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:12]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>C(#N)C>[O:10]=[C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:12]=1)[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 866910902-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone

Product 1

HCID 86691091t-butyl 2-(2-(2-oxo-2-(1-pentyl-1H-indol-3-yl)ethyl)phenoxy)acetateYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (O-desmethyl JWH-250) 5 (840 mg, 2.61 mmol) was dissolved in acetonitrile (20 ml) followed by the addition of potassium carbonate (1.08 g, 7.83 mmol) and t-butyl bromoacetate (0.76 g, 3.91 mmol). The reaction mixture was heated at reflux overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (Biotage Isolera 4, SNAP-25 g, 0%-10% ethyl acetate in hexane) to give 1.09 g (96%) of t-butyl 2-(2-(2-oxo-2-(1-pentyl-1H-indol-3-yl)ethyl)phenoxy)acetate (O-desmethyl JWH-250 t-Butyl 2-CME) 6.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography (Biotage Isolera 4, SNAP-25 g, 0%-10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-fe68be45c24349eca554a9c25ed8a5d8
Source dataset
uspto-grants-2016_09
Patent number
US09441033B2

Reaction notes

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