Sodium Hydroxide → 2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]benzenepropanoic acid

HRID 327936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327936
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:28]=[CH:27][C:21]2[C:22](=[O:26])[CH2:23][CH2:24][O:25][C:20]=2[C:19]=1[CH2:29][CH2:30][CH3:31].OC1C=CC2C(=O)CCOC=2C=1CCC.COC(=O)CCC1C=CC=CC=1CCCCCI.[OH-].[Na+]>CO>[O:26]=[C:22]1[C:21]2[CH:27]=[CH:28][C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[C:19]([CH2:29][CH2:30][CH3:31])[C:20]=2[O:25][CH2:24][CH2:23]1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 539299162-(5-Iodopentyl)benzenepropanoic acid methyl esterHCID 571435572-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]benzenepropanoic acid methyl ester

Produkt 1

HCID 199219552-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]benzenepropanoic acidAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Using the procedure of example 4, 2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]benzenepropanoic acid methyl ester was prepared, in 67.5% yield, starting from 0.35 g (1.69 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one and 0.54 g (1.5 mmol) of 2-(5-iodopentyl)benzenepropanoic acid methyl ester. A 0.5 g (1.14 mmol) sample of this ester was treated with 20 mL of methanol and 3 mL of aqueous 1N sodium hydroxide. The mixture was stirred and refluxed for 2.5 hr and then the solvent was removed in vacuo. The residue was diluted with water, acidified, and worked-up with ether in the usual manner. The product was recrystallized from hexane-ethyl acetate giving 2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]benzenepropanoic acid as a colorless solid, mp 94°-96° C., in 58.2% overall yield.

Aufarbeitung

  1. customwas prepared, in 67.5% yield
  2. temperaturerefluxed for 2.5 hr
  3. customthe solvent was removed in vacuo
  4. additionThe residue was diluted with water
  5. customThe product was recrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-27359e237adf4292927197e8fdece64f
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273999

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