Acetic Acid → 7-[2-(3-Hydroxy-3-pentyl-trans-1-propenyl)-5-hydroxy-cyclopentyl]-cis-4-heptenoic acid

HRID 866369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866369
[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])/[CH:3]=[CH:4]/[CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[CH:6]1[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][C:17]([OH:19])=[O:18].[BH4-].[Na+].C(O)(=O)C>CO>[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])/[CH:3]=[CH:4]/[CH:5]1[CH2:9][CH2:8][CH:7]([OH:10])[CH:6]1[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 867358317-[2-(3-Hydroxy-3-pentyl-trans-1-propenyl)-5-oxocyclopentyl]-cis-4-heptenoic acid

Produkt 1

HCID 867358307-[2-(3-Hydroxy-3-pentyl-trans-1-propenyl)-5-hydroxy-cyclopentyl]-cis-4-heptenoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

150 mg of 7-[2-(3-hydroxy-3-pentyl-trans-1-propenyl)-5-oxo-cyclopentyl]-cis-4-heptenoic acid were dissolved in 20 ml of methanol and three 150 mg portions of NaBH4 were added within the course 11/2 hours. The reaction solution was adjusted to pH 7 by means of glacial acetic acid, the solvent was removed by distillation under reduced pressure, the residue was acidified with 2N-HCl to pH 1 and extracted thrice with 150 ml of ether. After washing, the organic phase was concentrated.

Aufarbeitung

  1. customthe solvent was removed by distillation under reduced pressure
  2. extractionextracted thrice with 150 ml of ether
  3. washAfter washing
  4. concentrationthe organic phase was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-5a64b268a1f34ddeb92ce3ce79bcc28d
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04098815

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