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

HRID 357877Notes

Reaction equation

HRID 357877 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) δ 10.884 (bs, 1 H), 7.418-7.310 (m, 5 H), 7.231 (t, 2 H, J=7.5 Hz), 7.148-7.122 (m, 1 H), 7.071 (d, 2 H, J=7 Hz), 6.929 (t, 1 H, J=7.5 Hz), 6.843 (d, 1 H, J=7.5 Hz), 6.587 (d, 1 H, J=7.5 Hz), 6.545 (s, 1 H), 3.398 (AB, 2 H, JAB =15.5 Hz), 3.248 (d, 1 H, J=17 Hz), 3.125 (d, 1 H, J=17 Hz), 2.607-2.511 (m, 1 H), 2.338-2.159 (m, 3 H), 2.094 (s, 3 H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-4761b1ed33cc425a8a15402b32ba9eba
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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