Hydrochloric Acid → (1R,3S) 3-[(dihydro-2-oxo-3(2H)-thienylidene)-methyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid

HRID 648367Notes

Reaction equation

HRID 648367 reaction equation
[O:1]=[C:2]1[CH:6]([C@H:7]2[C@H:12]3[C@H:10]([C:11]3([CH3:14])[CH3:13])[C:9](=[O:15])[O:8]2)[CH2:5][CH2:4][S:3]1.Cl>C(N(CC)CC)C>[O:1]=[C:2]1[C:6](=[CH:7][C@H:12]2[C@@H:10]([C:9]([OH:15])=[O:8])[C:11]2([CH3:14])[CH3:13])[CH2:5][CH2:4][S:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22824566(1R,4R,5S) 4-[dihydro-2-oxo-3-(2H)-thienyl]-6,6-dimethyl-3-oxabicyclo-(3,1,0)-hexan-2-one

Product 1

HCID 54175652(1R,3S) 3-[(dihydro-2-oxo-3(2H)-thienylidene)-methyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of the solution of Step B and 6 ml of triethylamine was refluxed for 3 hours and was then cooled and poured into 2 N aqueous hydrochloric acid. The decanted organic phase was washed with water, dried and evaporated to dryness. The residue was taken up in 20 ml of hot methylene chloride and after the addition of 30 ml of n-heptane thereto, the mixture was cooled to 5° C. and vacuum filtered. The recovered product was washed with heptane and dried to obtain 3.025 g of (1R,3S) 3-[(dihydro-2-oxo-3(2H)-thienylidene)-methyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid melting at 162° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturewas then cooled
  3. washThe decanted organic phase was washed with water
  4. customdried
  5. customevaporated to dryness
  6. additionafter the addition of 30 ml of n-heptane
  7. filtrationvacuum filtered
  8. washThe recovered product was washed with heptane
  9. customdried

Sources & evidence

ORD record
ord-2a54d6c0424a4a2abab036d5a42c585c
Source dataset
uspto-grants-1983_10
Patent number
US04412069

Reaction notes

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