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

HRID 481915Notes

Reaction equation

HRID 481915 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) δ10.855 (bs, 1H), 7.395-7.306 (m, 5H), 7.115 (dd, 1H, J=1 Hz, J=7.5 Hz), 6.991 (t, 1H, J=7 Hz), 6.622 (td, 1H, J=1 Hz, J=7 Hz), 6.123 (d, 1H, J=7 Hz), 3.422 (s, 2H), 3.210-3.102 (m, 3H), 1.975-1.871 (m, 2H), 1.437-1.371 (m, 1H), 1.142-1.084 (m, 7H), 0.938-0.807 (m, 1H), 0.791-0.766 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-dbd978f38e0d4e478fcacd7f5951f364
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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