Ammonium Chloride → HCID 131737062, compound

HRID 59671Notes

Reaction equation

HRID 59671 reaction equation
Br[C:2]1(Br)[C@H:12]2[C@@H:3]1[CH2:4][O:5][C:6]1[C:11]2=[CH:10][CH:9]=[C:8]([CH2:13][O:14][CH3:15])[C:7]=1[C:16]([O:18][CH3:19])=[O:17].[Cl-].[NH4+]>C(O)C.[Zn]>[CH3:15][O:14][CH2:13][C:8]1[C:7]([C:16]([O:18][CH3:19])=[O:17])=[C:6]2[C:11]([C@H:12]3[CH2:2][C@H:3]3[CH2:4][O:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 25517Ammonium Chloride2×HCID 131737063HCID 131737063, compound2×

Product 1

HCID 131737062HCID 131737062, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 702EthanolSolvent

Procedure

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.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. stirringthe mixture was stirred
  4. temperatureheated
  5. temperatureat reflux overnight
  6. temperatureAfter cooling
  7. filtrationthe mixture was filtered through Celite
  8. customthe filtrate was evaporated to dryness
  9. customThe residue was partitioned between DCM and water
  10. dry with materialthe organic layer was dried (MgSO4)
  11. filtrationfiltered
  12. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c47ebe35ce674dd3a19712def066ec52
Source dataset
uspto-grants-2016_09
Patent number
US09440943B2

Reaction notes

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