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

HRID 481905Notes

Reaction equation

HRID 481905 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:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](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]=[C:33]([CH3:34])[CH:32]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 743753-Methylbenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 547217325,6-Dihydro-4-hydroxy-3-[(3-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), 3-methylbenzoyl chloride (0.12 mL, 0.89 mmol), CH2Cl2 (3.0 mL), acetonitrile (5.0 mL), acetone cyanohydrin (0.037 mL, 0.40 mmol), Et3N (0.24 mL, 1.8 mmol), glacial acetic acid (5.0 mL), sodium cyanoborohydride (0.16 g, 2.6 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 2% MeOH in CH2Cl2) to provide a solid (0.250 g, m.p. 53°-55° C.). 1H NMR (400 MHz, DMSO-d6) δ10.884 (bs, 1H), 7.418-7.310 (m, 5H), 7.231 (t, 2H, J=7.5 Hz), 7.148-7.122 (m, 1H), 7.071 (d, 2H, J=7 Hz), 6.929 (t, 1H, J=7.5 Hz), 6.843 (d, 1H, J=7.5 Hz), 6.587 (d, 1H, J=7.5 Hz), 6.545 (s, 1H), 3.398 (AB, 2H, JAB=15.5 Hz), 3.248 (d, 1H, J=17 Hz), 3.125 (d, 1H, J=17 Hz), 2.607-2.511 (m, 1H), 2.338-2.159 (m, 3H), 2.094 (s, 3H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-c925662fd4384cb1ac0b374b63170c0c
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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