반응 #87949

반응 방정식

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

수율 97.2%

용매

ethanol

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도at reflux for 6 hours
3. 3
   workup.STIRRINGthe mixture was stirred
4. 4
   온도heated
5. 5
   온도at reflux overnight
6. 6
   온도After cooling
7. 7
   여과the mixture was filtered through Celite
8. 8
   기타the filtrate was evaporated to dryness
9. 9
   기타The residue was partitioned between DCM and water
10. 10
    건조the organic layer was dried (MgSO4)
11. 11
    여과filtered
12. 12
    기타The filtrate was evaporated to dryness

실험 절차

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.

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