Réaction #68584

Équation de réaction

1.1′-(azodicarbonyl)dipiperidine

2-methoxyethanol

tri-n-butylphosphine

methoxymethanol

tert-butyl 2-(3-hydroxyquinolin-6-yl)acetate

→

desired product

tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate

Solvants

Hexane

benzene

Conditions de réaction

Traitement

1. 1
   Autreice bath was removed
2. 2
   Températurethe reaction mixture was warmed up to rt
3. 3
   workup.WAITAfter 2 h
4. 4
   Autreseparated out
5. 5
   Filtrationwas filtered off
6. 6
   ConcentrationThe filtrate was concentrated
7. 7
   AutreThe crude product was purified

Mode opératoire

To a suspension of tert-butyl 2-(3-hydroxyquinolin-6-yl)acetate (0.1 g, 0.4 mmol) in benzene (5 mL) was added 2-methoxyethanol (0.09 ml, 1 mmol) and tri-n-butylphosphine (0.1 ml, 0.6 mmol). The resulting mixture was cooled to 0° C. followed by adding 1.1′-(azodicarbonyl)dipiperidine (0.1 g, 0.6 mmol). After 10 min, ice bath was removed; the reaction mixture was warmed up to rt. After 2 h, TLC showed there still existed 50% starting material. More methoxymethanol (2 eq, 0.06 mL) was added. The reaction mixture was continued to stir for 20 h. Hexane was added to the reaction mixture and dihydro-ADDP separated out was filtered off. The filtrate was concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-027, 40 g SiO2, hexane:acetone=85%:15%, Flow=40 mL/min) to afford the desired product as colorless liquid. MS m/z: 318.4 (M+H). Calc'd. for C18H23NO4—317.38.

Source