Benzoic acid, 4-((5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl)-, ethyl ester → Ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-3-yl)ethynyl]benzoate

HRID 377349

Reaktionsgleichung

Reaktionsgleichung von HRID 377349
[BH4-].[Na+].[CH3:3][C:4]1([CH3:28])[C:13]2[CH:12]=[CH:11][C:10]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[CH:9][C:8]=2[C:7](=[O:27])[CH2:6][CH2:5]1>C1COCC1.C(O)C.O>[OH:27][CH:7]1[CH2:6][CH2:5][C:4]([CH3:3])([CH3:28])[C:13]2[CH:12]=[CH:11][C:10]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=3)=[CH:9][C:8]1=2

Komponenten

6

Edukt 2

HCID 3025901Benzoic acid, 4-((5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl)-, ethyl esterHCID 4311764Sodium borohydride2×

Produkt 1

HCID 3025972Ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-3-yl)ethynyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1 g (2.88 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 9) was converted into the title compound using 60 mg (1.6 mmol) of sodium borohydride. The procedure was as follows: To a cold solution (0° C.) of Compound 9 in 5 ml of THF and 10 ml of ethanol was added sodium borohydride. The mixture was stirred for 6 hours, diluted with water (10 ml) and extracted with Et2O (4×40 ml). The combined organic layers were washed with 10% HCl (5 ml), 10% aqueous NaHCO3 (10 ml) and brine (10 ml), dried over MgSo4 and concentrated in vacuo to give the title compound as a white solid.

Aufarbeitung

  1. extractionextracted with Et2O (4×40 ml)
  2. washThe combined organic layers were washed with 10% HCl (5 ml), 10% aqueous NaHCO3 (10 ml) and brine (10 ml)
  3. customdried over MgSo4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3c80e3025c104f179074e3370f6b2a62
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025388

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