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

HRID 357887Notes

Reaction equation

HRID 357887 reaction equation
[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.[CH:27]([C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=O)([CH3:29])[CH3:28].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[CH2:32][C:31]1[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=1[CH:27]([CH3:29])[CH3:28]

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 212225852-Isopropylbenzoyl chlorideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Product 1

HCID 547217485,6-Dihydro-4-hydroxy-3-[(2-isopropylphenyl)methyl]-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

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-isopropylbenzoyl chloride (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 (5.0 mL), sodium cyanoborohydride (0.50 g, 8.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2) to provide a solid (0.118 g, 124°-126° C.) . 1H NMR (400 MHz, DMSO-d6) δ 10.855 (bs, 1 H), 7.395-7.306 (m, 5 H), 7.115 (dd, 1 H, J=1 Hz, J=7.5 Hz), 6.991 (t, 1 H, J=7 Hz), 6.622 (td, I H, J=1 Hz, J=7 Hz), 6.123 (d, 1 H, J=7 Hz), 3.422 (s, 2 H), 3.210-3.102 (m, 3 H), 1.975-1.871 (m, 2 H), 1.437-1.371 (m, 1 H), 1.142-1.084 (m, 7 H), 0.938-0.807 (m, 1 H), 0.791-0.766 (m, 6 H).

Workup

  1. customPurification
  2. customto provide a solid (0.118 g, 124°-126° C.)

Sources & evidence

ORD record
ord-de089561c7f14dc78c3f8ea0b285337c
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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