تفاعل #87949

معادلة التفاعل

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

المردود 97.2%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةat reflux for 6 hours
3. 3
   workup.STIRRINGthe mixture was stirred
4. 4
   درجة الحرارةheated
5. 5
   درجة الحرارةat reflux overnight
6. 6
   درجة الحرارةAfter cooling
7. 7
   ترشيحthe mixture was filtered through Celite
8. 8
   أخرىthe filtrate was evaporated to dryness
9. 9
   أخرىThe residue was partitioned between DCM and water
10. 10
    تجفيفthe organic layer was dried (MgSO4)
11. 11
    ترشيحfiltered
12. 12
    أخرىThe filtrate was evaporated to dryness

الإجراء التجريبي

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.

المصدر