Acetone Cyanohydrin → 3-[(2-Chlorophenyl)methyl]-5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

HRID 357888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357888
[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.CCN(CC)CC.[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=O.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[CH2:30][C:3]1[C:4](=[O:19])[O:5][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)[CH2:7][C:2]=1[OH:1]

Komponenten

9

Edukt 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 691102-Chlorobenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Produkt 1

HCID 547217383-[(2-Chlorophenyl)methyl]-5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared as described in General Method 8 using the following: 5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 2-chlorobenzoyl chloride (0.15 mL, 1.15 mmol), CH2Cl2 (4.0 mL), acetonitrile (4.0 mL), acetone cyanohydrin (0.05 mL, 0.5 mmol), Et3N (0.35 mL, 2.5 mmol), glacial acetic acid (4.0 mL), sodium cyanoborohydride (0.720 g, 11.5 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2) to provide a solid (0.165 g, 51°-53° C.). 1H NMR (400 MHz, DMSO-d6) δ 11.062 (bs, 1 H), 7.425-7.275 (m, 6 H), 7.072 (td, 1 H, J=1.5 Hz, J=7.5 Hz), 6.774 (td, 1 H, J=1.2 Hz, J=7.5 Hz), 6.059 (dd, 1 H, J=1.2 Hz, J=7.5 Hz), 3.428 (AB, 2 H, JAB =16.5 Hz), 3.191 (AB, 2 H, JAB=17 Hz), 1.964-1.884 (m, 2 H), 1.450-1.384 (m, 1 H), 1.163-1.118 (m, 1 H), 0.951 (m, 1 H), 0.802-0.776 (m, 6 H).

Aufarbeitung

  1. customPurification
  2. customto provide a solid (0.165 g, 51°-53° C.)

Quellen und Nachweise

ORD-Eintrag
ord-b35efd8e05f749a2bbdbff58ea00606c
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840751

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