Lithium Hydroxide → 4-((5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid

HRID 1229

Reaktionsgleichung

Reaktionsgleichung von HRID 1229
[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)[CH:8]=[CH:7][C:6]=2[C:5](=[O:25])[CH2:4][CH2:3]1.[Li+].[OH-]>C1COCC1.C(O)C>[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=3)[CH:8]=[CH:7][C:6]=2[C:5](=[O:25])[CH2:4][CH2:3]1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 15345545Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate2×

Produkt 1

HCID 153455474-((5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 0.30 g (0.87 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 4 ml of THF and 2 ml of ethanol was added 2 ml (2 mmol) of LiOH (1N aqueous solution). The reaction mixture was stirred at room temperature for 4 hours, concentrated in vacuo to near dryness, partitioned between EtOAc and 1 ml of water and acidified to pH 4 with 10% HCl. The aqueous layer was extracted with EtOAc and then the organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. custompartitioned between EtOAc and 1 ml of water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a7c746e75636433f9e27f8624b0dcadb
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723620

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