Acetone Cyanohydrin → 5,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-3-phenylmethyl-2H-pyran-2-one

HRID 357883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357883
[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.[C:27](Cl)(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[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][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

9

Edukt 5

HCID 6406Acetone CyanohydrinHCID 7412Benzoyl chlorideHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Produkt 1

HCID 547216415,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-3-phenylmethyl-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), benzoyl chloride (0.13 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 (0.51 g, 8.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2 Cl2) to provide a solid (0.215 g, 46°-48° C.). 1H NMR (400 MHz, DMSO-d6) δ 10.864 (bs, 1 H), 7.375-7.248 (m, 7 H), 7.026-7.000 (m, 2 H), 6.737-6.713 (m, 1 H), 3.393-3.332 (2 H, obscurred by solvent), 3.110 (AB, 2 H, JAB =17 Hz), 1.933-1.870 (m, 2 H), 1.402-1.353 (m, 1 H), 1.132-1.084 (m, 1 H), 0.891-0.710 (m, 7 H).

Aufarbeitung

  1. customPurification
  2. customto provide a solid (0.215 g, 46°-48° C.)

Quellen und Nachweise

ORD-Eintrag
ord-1c16219aaca24809bac2c3526f5e14d2
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840751

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