Potassium Carbonate → HCID 86729296, compound

HRID 1051534Notes

Reaction equation

HRID 1051534 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH:4]=[CH:3][CH:2]=1.Cl[CH2:19][C@@H:20]1[CH2:22][O:21]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[O:21]1[CH2:22][C@@H:20]1[CH2:19][O:17][C:13]1[CH:12]=[C:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149428(+)-EpichlorohydrinHCID 20816513HCID 20816513, compound

Product 1

HCID 86729296HCID 86729296, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(quinolin-8-yl)phenol (221 mg, 1 mmol) and (S)-2-(chloromethyl)oxirane (114.6 mg, 1.2 mmol) in CH3CN (10 mL) was added K2CO3 (690 mg, 5 mmol). The reaction mixture was stirred at 80° C. for 4 h. The solid was removed by filtration and the filtrate was concentrated to yield a crude (R)-8-(3-(oxiran-2-ylmethoxy)phenyl)quinoline which was used in the next step without further purification. (210 mg, Yield 75%). LCMS (m/z): 278.1 (M+1).

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2063ebfc42104063be014f296a979ed6
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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