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

HRID 357882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357882
[OH:1][C:2]1[CH2:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[O:5][C:4](=[O:19])[CH:3]=1.CCN(CC)CC.[CH3:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=O.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]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:5][C:4](=[O:19])[C:3]=1[CH2:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:30]([CH3:31])[CH:29]=1

Komponenten

9

Edukt 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 743753-Methylbenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Produkt 1

HCID 547216225,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-3-[(3-methylphenyl)methyl]-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-phenyl-6-(3-methylbutyl)-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 3-methylbenzoyl 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 (0.51 g, 8.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 0.5% MeOH in CH2Cl2) to provide a solid (0.252 g, 53°-55° C.). 1H NMR (400 MHz, DMSO-d6) δ 7.376-7.244 (m, 5 H), 6.915 (t, 1 H, J=7.5 Hz), 6.831 (d, 1 H, J=7.5 Hz), 6.549 (d, 1 H, J=7.5 Hz), 6.509 (s, 1 H), 3.369 (AB, 2 H, JAB =14.4 Hz), 3.112 (AB, 2 H, JAB =17.5 Hz), 2.088 (s, 3 H), 1.962 (m, 2 H), 1.416-1.333 (m, 1 H), 1.152-1.061 (m, 1 H), 0.898-0.726 (m, 7 H).

Aufarbeitung

  1. customPurification
  2. customto provide a solid (0.252 g, 53°-55° C.)

Quellen und Nachweise

ORD-Eintrag
ord-eba171c9b7bc4fb89265d025d0ff42f0
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840751

Notizen zur Reaktion

Wird geladen…