Acetic Acid → HCID 86740326, compound

HRID 569539Notes

Reaction equation

HRID 569539 reaction equation
Cl.[CH3:2][C:3]1([CH3:30])[C@@H:5](/[CH:6]=[CH:7]\[C:8](=[O:10])[OH:9])[C@H:4]1[C:11]([O:13][CH:14]([C:28]#[N:29])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)=[O:12].C(O)(=O)C.[O:35]1[CH:40]=[CH:39][CH2:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[Ca+2]>C(Cl)Cl>[CH3:2][C:3]1([CH3:30])[C@@H:5](/[CH:6]=[CH:7]\[C:8](=[O:9])[O:10][CH:36]2[CH2:37][CH2:38][CH2:39][CH2:40][O:35]2)[C@H:4]1[C:11]([O:13][CH:14]([C:28]#[N:29])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)=[O:12]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 10112Calcium CarbonateHCID 86740327HCID 86740327, compound

Product 1

HCID 86740326HCID 86740326, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A methanolic N hydrochloric acid solution was added dropwise at 15° C. with stirring to a mixture of 1.5 g of α-cyano-3-phenoxy-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate solvated with one mole of acetic acid, 4.5 ml of dihydropyran and 10 ml of methylene chloride and the mixture was stirred at room temperature for 30 minutes. Calcium carbonate was added to the mixture which was then filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8-2 hexane-ether mixture yielded 1.07 g of α-cyano-3-phenoxy-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(tetrahydropyran-2-yloxy)-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+47° (c=0.5% in benzene).

Workup

  1. filtrationwas then filtered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was chromatographed over silica gel
  4. washElution with an 8-2 hexane-ether mixture

Sources & evidence

ORD record
ord-6ea3aea4abff4b78923855ccfc4270ce
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

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