Acetone Cyanohydrin → 5,6-Dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-3-phenylmethyl-2H-pyran-2-one

HRID 481903Notes

Reaction equation

HRID 481903 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.[C:30](Cl)(=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.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:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 7412Benzoyl chlorideHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 547215815,6-Dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-3-phenylmethyl-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 (0.26 mL, 1.94 mmol), benzoyl chloride (0.109 mL, 0.94 mmol), CH2Cl2 (2.0 mL), acetonitrile (5.0 mL), acetone cyanohydrin (0.04 mL, 0.43 mmol), Et3N (0.26 mL, 1.9 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 CH2 Cl2) to provide a thick oil (0.384 g). 1H NMR (400 MHz, DMSO-d6) δ10.922 (bs, 1H), 7.395-7.315 (m, 5H), 7.297-7.126 (m, 3H), 7.084-7.028 (m, 5H), 6.775-6.611 (m, 2H), 3.423 (s, 2H), 3.248 (d, 1H, J=17 Hz), 3.175 (d, 1H, J=17 Hz), 2.619-2.551 (m, 1H), 2.292-2.227 (m, 3H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-1e0818a41b3e4feba44b159566d172d8
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

Loading…