Hydrochloric Acid → 3-Hydroxy-5,6-dihydro-naphthalene-2-carbonitrile

HRID 131169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131169
[OH:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]2[C:6](=O)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[Li+].[BH4-].O.Cl>C1COCC1.CO>[OH:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]2[CH:6]=[CH:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 218649643-Hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Produkt 1

HCID 218649383-Hydroxy-5,6-dihydro-naphthalene-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To the suspension of 3-hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile from (150 mg, 0.8 mmol) in 2 mL anhydrous THF was added 2M LiBH4 in THF (0.6 mL, 1.2 mmol, 1.5 eq) and 0.5 mL anhydrous methanol. The reaction was shaken at 40° C. for 2 h. To this was added 5 mL water and some 1N HCl until pH=2. The mixture was extracted with ethyl acetate 3 times and dried down with genavac at high temperature. The resulting dark liquid (about 100 mg) was used directly in the next step reaction.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate 3 times
  2. customdried down with genavac at high temperature
  3. customThe resulting dark liquid (about 100 mg) was used directly in the next step reaction

Quellen und Nachweise

ORD-Eintrag
ord-dc69b1eeb64f4d48a500d1c0213c9834
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384947B2

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