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

HRID 357888Notes

Reaction equation

HRID 357888 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.[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=O.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[CH2:30][C:3]1[C:4](=[O:19])[O:5][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)[CH2:7][C:2]=1[OH:1]

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 691102-Chlorobenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Product 1

HCID 547217383-[(2-Chlorophenyl)methyl]-5,6-dihydro-4-hydroxy-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-chlorobenzoyl 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 (0.720 g, 11.5 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2) to provide a solid (0.165 g, 51°-53° C.). 1H NMR (400 MHz, DMSO-d6) δ 11.062 (bs, 1 H), 7.425-7.275 (m, 6 H), 7.072 (td, 1 H, J=1.5 Hz, J=7.5 Hz), 6.774 (td, 1 H, J=1.2 Hz, J=7.5 Hz), 6.059 (dd, 1 H, J=1.2 Hz, J=7.5 Hz), 3.428 (AB, 2 H, JAB =16.5 Hz), 3.191 (AB, 2 H, JAB=17 Hz), 1.964-1.884 (m, 2 H), 1.450-1.384 (m, 1 H), 1.163-1.118 (m, 1 H), 0.951 (m, 1 H), 0.802-0.776 (m, 6 H).

Workup

  1. customPurification
  2. customto provide a solid (0.165 g, 51°-53° C.)

Sources & evidence

ORD record
ord-b35efd8e05f749a2bbdbff58ea00606c
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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