Phenylacetyl chloride → 5,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-3-(2-phenylethyl)-2H-pyran-2-one

HRID 481876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481876
[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[CH:3]=1.[C:20]1([CH2:26][C:27](Cl)=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.C1COCC1>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:5][C:4](=[O:19])[C:3]=1[CH2:27][CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

7

Edukt 4

HCID 7679Phenylacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Produkt 1

HCID 547216245,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-3-(2-phenylethyl)-2H-pyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

The title compound was prepared as described in General Method 5 using 2.0 mmol of 5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one, 2.1 mmol of phenylacetyl chloride, 2.1 mmol of triethylamine, and 10 mL of THF, followed by 10 mL of toluene and catalytic DMAP. Chromatography of the residue afforded 1.0 mmol of the intermediate acyl compound. Reduction of this intermediate was effected with 2 mmol of sodium cyanoborohydride. The product was obtained as a solid (m.p. 125°-126° C.). 1H NMR (DMSO-d6) δ0.76 (m, 7H), 1.12 (m, 1H), 1.38 (m, 1H), 1.87 (m, 2H), 2.27-2.46 (m, 4H), 2.97 (q, 2H), 6.98-7.38 (m, 10H).

Quellen und Nachweise

ORD-Eintrag
ord-50c3bfb7b578480ba216e5cd6e695ee0
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789440

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