تفاعل #1622234

معادلة التفاعل

sodium bicarbonate

Methanesulfonic acid

6-[3-(carbomethoxy-2-methoxyquinolin-7-yl)thiopropyl]-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran

trifluoroacetic acid

thioanisole

→

2-phenylethyl-2,3-dihydrobenzofuran

المذيبات

brine

diethyl ether

tetrahydrofurane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe organic layer was separated
2. 2
   تجفيفdried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe residue was chromatographed on silica gel using 30% ethyl acetate in hexane as eluent

الإجراء التجريبي

Methanesulfonic acid (0.5 mL) was added dropwise to a solution of 6-[3-(carbomethoxy-2-methoxyquinolin-7-yl)thiopropyl]-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E25, (1.1 gm; 1.7 mmoles), trifluoroacetic acid (11 mL) and thioanisole (3 mL) at 5° C. The mixture was stirred for 30 minutes and then added in portions to an ice cold stirring biphasic mixture of saturated sodium bicarbonate solution (150 mL), brine (25 mL), tetrahydrofurane (125 mL) and diethyl ether (25 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel using 30% ethyl acetate in hexane as eluent to yield 900 mgs (95%) of 6-[3-(3-carbomethoxy-2-methoxyquinolin-7-yl)thiopropyl]-5-hydroxy-2-(2-phenylethyl-2,3-dihydrobenzofuran, E26, that had crystallized from diethyl ether, m.p. 112°-114° C.

المصدر