反応 #87949

反応方程式

methyl cis-(1aRS,7bSR)-1,1-dibromo-5-methoxymethyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Intermediate 8

methyl cis-(1aRS,7bSR)-1,1-dibromo-5-methoxymethyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

ammonium chloride

ammonium chloride

→

methyl cis-(1aRS,7bSR)-5-methoxymethyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

収率 97.2%

溶媒

ethanol

反応条件

後処理

1. 1
   温度heated
2. 2
   温度at reflux for 6 hours
3. 3
   workup.STIRRINGthe mixture was stirred
4. 4
   温度heated
5. 5
   温度at reflux overnight
6. 6
   温度After cooling
7. 7
   ろ過the mixture was filtered through Celite
8. 8
   その他the filtrate was evaporated to dryness
9. 9
   その他The residue was partitioned between DCM and water
10. 10
    乾燥the organic layer was dried (MgSO4)
11. 11
    ろ過filtered
12. 12
    その他The filtrate was evaporated to dryness

実験手順

A mixture of methyl cis-(1aRS,7bSR)-1,1-dibromo-5-methoxymethyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 8, 1.06 g), zinc dust (4.14 g), and ammonium chloride (1.75 g) in absolute ethanol (100 mL) was stirred and heated at reflux for 6 hours. Further zinc dust (2.0 g) and ammonium chloride (0.9 g) were added and the mixture was stirred and heated at reflux overnight. After cooling, the mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was partitioned between DCM and water and the organic layer was dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl cis-(1aRS,7bSR)-5-methoxymethyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.63 g) as an oil.

出典