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

HRID 481916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481916
[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) δ11.062 (bs, 1H), 7.425-7.275 (m, 6H), 7.072 (td, 1H, J=1.5 Hz, J=7.5 Hz), 6.774 (td, 1H, J=1.2 Hz, J=7.5 Hz), 6.059 (dd, 1H, J=1.2 Hz, J=7.5 Hz), 3.428 (AB, 2H, JAB =16.5 Hz), 3.191 (AB, 2H, JAB=17 Hz), 1.964-1.884 (m, 2H), 1.450-1.384 (m, 1H), 1.163-1.118 (m, 1H), 0.951 (m, 1H), 0.802-0.776 (m, 6H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1d7ab3c94c704199b63e636fa5f9124a
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789440

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