Acetone Cyanohydrin → 4-hydroxy-5-[(3-methoxyphenyl)methyl]-2-phenethyl-2-phenyl-3H-pyran-6-one

HRID 481913Notes

Reaction equation

HRID 481913 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[CH:3]=1.[CH3:23]CN(CC)CC.[CH3:30][O:31][C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1C(Cl)=O.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:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[C:3]=1[CH2:23][C:39]1[CH:38]=[CH:37][CH:33]=[C:32]([O:31][CH3:30])[CH:40]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 889692-Methoxybenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 547140764-hydroxy-5-[(3-methoxyphenyl)methyl]-2-phenethyl-2-phenyl-3H-pyran-6-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-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (0.300 g, 1.02 mmol), Et3N (0.15 mL, 1.1 mmol), 2-methoxybenzoyl chloride (0.17 g, 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 (0.47 g, 7.5 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2Cl2) to provide a solid (0.227 g, 62°-64° C.). 1H NMR (400 MHz, DMSO-d6) δ10.823 (bs, 1H), 7.436-7.362 (m, 5H), 7.265 (t, 2H, 7.176-7.098 (m, 3H), 7.022 (td, 1H, J=1 Hz, J=8 Hz), 6.815 (d, 1H, J=7.5 Hz), 6.400 (td, 1H, J=1 Hz, J=7.5 Hz), 5.952 (dd, 1H, J=1 Hz, J=7 Hz), 3.716 (s, 3H), 3.391-3.169 (m, 4H), 2.650-2.582 (m, 1H), 2.354-2.182 (m, 3H).

Workup

  1. customPurification
  2. customto provide a solid (0.227 g, 62°-64° C.)

Sources & evidence

ORD record
ord-8fe67b75643e4682a7212801c2a8da21
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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