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

HRID 357883Notes

Reaction equation

HRID 357883 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[CH:3]=1.CCN(CC)CC.[C:27](Cl)(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:5][C:4](=[O:19])[C:3]=1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 7412Benzoyl chlorideHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Product 1

HCID 547216415,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-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-(3-methylbutyl)-6-phenyl-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), benzoyl chloride (0.13 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 (0.51 g, 8.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2 Cl2) to provide a solid (0.215 g, 46°-48° C.). 1H NMR (400 MHz, DMSO-d6) δ 10.864 (bs, 1 H), 7.375-7.248 (m, 7 H), 7.026-7.000 (m, 2 H), 6.737-6.713 (m, 1 H), 3.393-3.332 (2 H, obscurred by solvent), 3.110 (AB, 2 H, JAB =17 Hz), 1.933-1.870 (m, 2 H), 1.402-1.353 (m, 1 H), 1.132-1.084 (m, 1 H), 0.891-0.710 (m, 7 H).

Workup

  1. customPurification
  2. customto provide a solid (0.215 g, 46°-48° C.)

Sources & evidence

ORD record
ord-1c16219aaca24809bac2c3526f5e14d2
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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