Acetone Cyanohydrin → 3-[(2-Chlorophenyl)methyl]-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one
Reaction equation
[OH:1][C:2]1[CH2:7][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:20])[CH:3]=1.CCN(CC)CC.[Cl:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=O.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[Cl:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[CH2:31][C:3]1[C:4](=[O:20])[O:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][C:2]=1[OH:1]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
The title compound was prepared as described in General Method 8 using the following: 5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (0.300 g, 1.13 mmol), Et3N (0.17 mL, 1.2 mmol), 2-chlorobenzoyl chloride (0.14 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 (0.50 g, 7.9 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 0.5% MeOH in CH2 Cl2) to provide a solid (0.130 g, 185°-187° C.). 1H NMR (400 MHz, DMSO-d6) δ11.351 (bs, 1H), 7.464-7.282 (m, 11H), 7.054 (t, 1H, J=7 Hz), 6.679 (td, 1H, J=1 Hz, J=7.5 Hz), 5.797 (d, 1H, J=7 Hz), 3.586 (s, 2H), 3.472 (s, 2H).
Workup
- customPurification
- customto provide a solid (0.130 g, 185°-187° C.)
Sources & evidence
- ORD record
- ord-2df3c086cbee41a5b1bb1f5274640f41
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789440
Reaction notes
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