Reaktion #69698

Reaktionsgleichung

(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-(5-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone

1-chloro-2-methoxy-ethane

1-chloro-2-methoxy-ethane

K2CO3

K2CO3

→

title compound

Ausbeute 104.2%

(2,4-bis-benzyloxy-5-isopropyl-phenyl)-[5-(2-methoxy-ethoxy)-1,3-dihydro-isoindol-2-yl]-methanone

Ausbeute 104.2%

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen heated at 90° C. for 16 hours
2. 2
   SonstigeReaction
3. 3
   Temperaturcooled to room temperature
4. 4
   Filtrationthen filtered
5. 5
   Sonstigethen purified by flash column chromatography
6. 6
   Wascheneluting with 100% petroleum ether to 100% ethyl acetate

Vorschrift

(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-(5-hydroxy-1,3-dihydro-isoindol-2-yl)-methanone (A2 from 2,4-bis-benzyloxy-5-isopropyl-benzoic acid (Preparation B10) and 5-hydroxyisoindoline) (100 mg, 0.2 mmol), 1-chloro-2-methoxy-ethane (23.6 mg, 0.25 mmol) and K2CO3 (34.5 mg, 0.25 mmol) in DMF (4 ml) were combined and stirred for 2 hours at room temperature. A further 0.25 mmol of 1-chloro-2-methoxy-ethane and K2CO3 was added then heated at 90° C. for 16 hours. Reaction cooled to room temperature and diluted with EtOAc then filtered. The filtrate was reduced in vacuo then purified by flash column chromatography, eluting with 100% petroleum ether to 100% ethyl acetate to afford 115 mg of the title compound as a colourless gel. MS: [M+H]+ 552

Quelle