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

HRID 481916Notes

Reaction equation

HRID 481916 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) δ11.062 (bs, 1H), 7.425-7.275 (m, 6H), 7.072 (td, 1H, J=1.5 Hz, J=7.5 Hz), 6.774 (td, 1H, J=1.2 Hz, J=7.5 Hz), 6.059 (dd, 1H, J=1.2 Hz, J=7.5 Hz), 3.428 (AB, 2H, JAB =16.5 Hz), 3.191 (AB, 2H, JAB=17 Hz), 1.964-1.884 (m, 2H), 1.450-1.384 (m, 1H), 1.163-1.118 (m, 1H), 0.951 (m, 1H), 0.802-0.776 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-1d7ab3c94c704199b63e636fa5f9124a
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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