Trifluoroacetic acid → 2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone

HRID 61309Notes

Reaction equation

HRID 61309 reaction equation
[O:1]=[C:2]([C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:20]=1)[CH2:3][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6]CC(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[OH:6][C:5]1[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=1[CH2:3][C:2]([C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:20]=1)=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691091t-butyl 2-(2-(2-oxo-2-(1-pentyl-1H-indol-3-yl)ethyl)phenoxy)acetate2×

Product 1

HCID 866910902-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanoneYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (1.09 g, 2.50 mmol) was dissolved in dichloromethane (20 ml) and trifluoroacetic acid (10 ml) was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 50% ethyl acetate in hexane) to give 512 mg (54%) of O-desmethyl JWH-250 2-CME (Hapten 1) as a tan solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-786b7da843d2405b9b0be44890d3e808
Source dataset
uspto-grants-2016_09
Patent number
US09441033B2

Reaction notes

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