Acetyl chloride → methyl cis-(1aRS,7bSR)-5-chloromethyl-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate

HRID 59670Notes

Reaction equation

HRID 59670 reaction equation
CO[CH2:3][C:4]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]2[C:7]([C@H:8]3[CH2:18][C@H:9]3[CH2:10][O:11]2)=[CH:6][CH:5]=1.C([Cl:22])(=O)C>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[Cl:22][CH2:3][C:4]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]2[C:7]([C@H:8]3[CH2:18][C@H:9]3[CH2:10][O:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 131737062HCID 131737062, compound2×

Product 1

HCID 131737061methyl cis-(1aRS,7bSR)-5-chloromethyl-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Zinc chloride (0.014 g) was added to a solution of methyl cis-(1aRS,7bSR)-5-methoxymethyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 7, 0.53 g) and acetyl chloride (0.77 mL) in anhydrous diethyl ether (50 mL) and the resultant mixture was stirred for 1.5 hours. The mixture was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl cis-(1aRS,7bSR)-5-chloromethyl-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (0.486 g) as a gum.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-96761a42c1b54b4ead90af2c0ab849dc
Source dataset
uspto-grants-2016_09
Patent number
US09440943B2

Reaction notes

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