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

HRID 481904Notes

Reaction equation

HRID 481904 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.CCN(CC)CC.[CH3:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](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[CH2:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[CH3:33]

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 702762-Methylbenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 547216095,6-Dihydro-4-hydroxy-3-[(2-methylphenyl)methyl]-6-phenyl-6-(2-phenylethyl)-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-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (0.250 g, 0.850 mmol), Et3N (0.12 mL, 0.85 mmol), 2-methylbenzoyl chloride (0.11 mL, 0.85 mmol), CH2Cl2 (5.0 mL), acetonitrile (4.0 mL), acetone cyanohydrin (0.04 mL, 0.43 mmol), Et3N (0.24 mL, 1.7 mmol), glacial acetic acid (10.0 mL), sodium cyanoborohydride (0.151 g, 2.4 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 2% MeOH in CH2Cl2) to provide a solid (0.195 g, m.p. 109°-111° C.). 1H NMR (400 MHz, DMSO-d6) δ10.886 (bs, 1H), 7.457-7.359 (m, 5H), 7.242 (t, 2H, J=7 Hz), 7.169-7.130 (m, 1H), 7.097 (d, 2H, J=7.5 Hz), 7.001 (d, 1H, J=7.5 Hz), 6.937 (t, 1H, J=7.5 Hz), 6.695 (t, 1H, J=7 Hz), 6.215 (d, 1H, J=7.5 Hz), 3.292 (d, 1H, J=17 Hz), 3.169 (d, 1H, J=17 Hz), 2.643-2.584 (m, 1H), 2.50-2.475 (2H+solvent) 2.296-2.182 (m, 3H), 2.125 (s, 3H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-25c89235b6504067a9adeb2c335650c2
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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