Hydrochloric Acid → HCID 68148620, compound

HRID 1579140Notes

Reaction equation

HRID 1579140 reaction equation
Cl.[OH:2][C@@H:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:4]=[CH:5][CH:6]1[CH:10]=[CH:9][C:8](=[O:11])[CH:7]1[CH2:12][CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]>C(O)C>[OH:2][C@@H:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:4]=[CH:5][CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH:7]1[CH2:12][CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68149236HCID 68149236, compound

Product 1

HCID 68148620HCID 68148620, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

After 25 hours of growth, the pH of the flasks is adjusted to 6.7 with 5 N HCl. Forty mg. of 7-(2-[(3S)-3-hydroxy-1-octenyl]-5-oxo-3-cyclopenten-1-yl)-5-heptenoic acid diluted in 2 ml. of ethanol is added to each one liter flask, and 20 mg. in one ml. of ethanol is added to the single 500 ml. flask. The flasks are put under N2 and incubated as above. Following 22.5 hours of shaking, the flasks are harvested. The mixture is filtered and the filtrate acidified with acetic acid and extracted with ether. After washing and drying, the filtrate is evaporated and the resulting residue chromatographed on silica. Elution with 40% ethyl acetate in hexane affords 0.42 g. of the title product. I.R. Analysis: λmaxfilm 3.0 (shoulder), 3.4, 5.7, 7.05, 8.1, 8.6, 10.3μ .

Workup

  1. waitFollowing 22.5 hours
  2. filtrationThe mixture is filtered
  3. extractionextracted with ether
  4. washAfter washing
  5. customdrying
  6. customthe filtrate is evaporated
  7. customthe resulting residue chromatographed on silica
  8. washElution with 40% ethyl acetate in hexane
  9. customaffords 0.42 g

Sources & evidence

ORD record
ord-59c75b991d2640a281964aa7a2bbfa2f
Source dataset
uspto-grants-1976_01
Patent number
US03930952

Reaction notes

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