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

HRID 481909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481909
[OH:1][C:2]1[CH2:7][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:20])[CH:3]=1.CCN(CC)CC.[CH:28]([C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](Cl)=O)([CH3:30])[CH3:29].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]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:5][C:4](=[O:20])[C:3]=1[CH2:33][C:32]1[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=1[CH:28]([CH3:30])[CH3:29]

Komponenten

9

Edukt 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 212225852-Isopropylbenzoyl chlorideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Produkt 1

HCID 547216355,6-Dihydro-4-hydroxy-3-[(2-isopropylphenyl)methyl]-6,6-diphenyl-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-6,6-diphenyl-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 2-isopropylbenzoyl chloride (1.02 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 (5.0 mL), sodium cyanoborohydride (0.50 g, 8.5 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 (0.128 g, 224°-226° C.). 1H NMR (400 MHz, DMSO-d6) δ11.180 (bs, 1H), 7.445-7.235 (m, 10H), 7.109 (d, 1H, J=7.5 Hz), 6.970 (t, 1H, J=7.5 Hz), 6.515 (t, 1H, J=7.5 Hz), 5.841 (d, 1H, J=7.5 Hz), 3.560 (s, 2H), 3.463 (s, 2H), 1.174-1.094 (m, 7H).

Aufarbeitung

  1. customPurification
  2. customto provide a solid (0.128 g, 224°-226° C.)

Quellen und Nachweise

ORD-Eintrag
ord-7446ed9c48e24865a46ea6efe6d5729d
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789440

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