反応 #552616

反応方程式

methyl 5-[4-acetonylphenoxymethyl]furan-2-carboxylate

2-hydroxy-2-(3-chlorophenyl) ethanamine

water

→

methyl 5-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]furan-2-carboxylate

溶媒

benzene

反応条件

後処理

1. 1
   温度was heated
2. 2
   その他The solvent was evaporated
3. 3
   workup.ADDITIONsodium borohydride (2 g) added, in portions, to a stirred solution of the residual oil in methanol (80 ml)
4. 4
   温度with cooling in ice
5. 5
   その他the solvent was evaporated
6. 6
   その他the residue was partitioned between water and dichloromethane
7. 7
   乾燥The organic layer was dried (MgSO4)
8. 8
   その他evaporated to an oil which
9. 9
   その他was purified by column chromatography on silica gel
10. 10
    洗浄Elution with methanol:chloroform (4:96)
11. 11
    その他gave an oil which
12. 12
    その他was crystallised from n-hexane

実験手順

A mixture of methyl 5-[4-acetonylphenoxymethyl]furan-2-carboxylate (1.76 g) and 2-hydroxy-2-(3-chlorophenyl) ethanamine (1.05 g) in dry benzene (100 ml) was heated under reflux with azeotropic removal of water, for 2 hr. The solvent was evaporated and sodium borohydride (2 g) added, in portions, to a stirred solution of the residual oil in methanol (80 ml) with cooling in ice. The mixture was stirred at ambient temperature for 3 hr. the solvent was evaporated and the residue was partitioned between water and dichloromethane. The organic layer was dried (MgSO4) and evaporated to an oil which was purified by column chromatography on silica gel. Elution with methanol:chloroform (4:96) gave an oil which was crystallised from n-hexane to give methyl 5-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]furan-2-carboxylate, m.pt 75°-86° C., as a 19:81 mixture of diastereoisomers. The mother liquor was evaporated; crystallisation from Petroleum ether (60:80)--ether gave a second crop, m.pt. 75°-83° C., as a 55:45 mixture of diastereoisomers.

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