Hydrochloric Acid → HCID 86739224, compound

HRID 1388258Notes

Reaction equation

HRID 1388258 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1([CH3:19])[C@H:10](/[CH:11]=[CH:12]/[C:13](=[O:15])[CH3:14])[C@H:9]1[C:16](Cl)=[O:17].[CH2:20]([OH:22])[CH3:21].Cl>C1C=CC=CC=1>[CH3:7][C:8]1([CH3:19])[C@H:10](/[CH:11]=[CH:12]/[C:13](=[O:15])[CH3:14])[C@H:9]1[C:16]([O:22][CH2:20][CH3:21])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1049PyridineHCID 131713381HCID 131713381, compound

Product 1

HCID 86739224HCID 86739224, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2 ml of pyridine, 2.9 g of (1R,trans) 2,2-dimethyl-3-[(E)-3-oxo-1-butenyl]-cyclopropane-1-carboxylic acid chloride, 1 ml of ethanol and 25 ml of benzene was stirred at 0° to 5° C. for 20 minutes and at room temperature for 2 hours and was then poured into iced aqueous N/6 hydrochloric acid solution. The mixture was extracted with ether and the organic phase was washed with water, dried and evaporated to dryness at 40° C. under reduced pressure. The 4.19 g of oil residue were chromatographed over silica gel and eluted with a 7-3 cyclohexane-ethyl acetate mixture to obtain 1.43 g of ethyl (1R,trans) 2,2-dimethyl-3-[(E)-3-oxo-1-butenyl]-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =+82°±3° (c=0.5% in benzene).

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness at 40° C. under reduced pressure
  5. customThe 4.19 g of oil residue were chromatographed over silica gel
  6. washeluted with a 7-3 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-cf246ed9bb4b4bbe8ac82a5a5eb9893c
Source dataset
uspto-grants-1984_02
Patent number
US04431576

Reaction notes

Loading…