2-Chloroethanol → 5-(2-Chloroethoxy)quinoline

HRID 1250167Notes

Reaction equation

HRID 1250167 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:31][CH2:32][CH2:33]O.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1.O>[Cl:31][CH2:32][CH2:33][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 4

HCID 342-Chloroethanol2×HCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 135441757Quinolin-5-ol

Product 1

HCID 117890025-(2-Chloroethoxy)quinolineYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 100 ml three-neck oven dry flask was cooled under nitrogen. 5-Hydroxy quinoline (2 g, 14 mmol) was added as well as triphenylphosphine (5.42 g, 21 mmol) suspended in 50 ml anhydrous tetrahydrofuran. 2-Chloroethanol (1.3 ml, 21 mmol) was slowly added to above reaction mixture via syringe, followed by adding DEAD (2.98 ml, 21 mmol) via syringe. A second 1.5 eq of 2-chloroethanol, triphenylphosphine and DEAD was added. The reaction mixture was poured into 100 ml water and extracted by methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatographed (20% ethyl acetate-hexanes) afforded 2.31 g (82%) of product as a solid: mp 75-78° C.

Workup

  1. customA 100 ml three-neck oven dry flask
  2. temperaturewas cooled under nitrogen
  3. extractionextracted by methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customChromatographed (20% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-a38bd28523444c53953ac94759f3a5e2
Source dataset
uspto-grants-2002_01
Patent number
US06337336B1

Reaction notes

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