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

HRID 481910Notes

Reaction equation

HRID 481910 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[O:5][C:4](=[O:19])[CH:3]=1.CCN(CC)CC.[CH3:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](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]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:5][C:4](=[O:19])[C:3]=1[CH2:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:30]([CH3:31])[CH:29]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 743753-Methylbenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Product 1

HCID 547216225,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-3-[(3-methylphenyl)methyl]-6-phenyl-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-(3-methylbutyl)-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 3-methylbenzoyl chloride (0.15 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 0.5% MeOH in CH2Cl2) to provide a solid (0.252 g, 53°-55° C.). 1H NMR (400 MHz, DMSO-d6) δ7.376-7.244 (m, 5H), 6.915 (t, 1H, J=7.5 Hz), 6.831 (d, 1H, J=7.5 Hz), 6.549 (d, 1H, J=7.5 Hz), 6.509 (s, 1H), 3.369 (AB, 2H, JAB =14.4 Hz), 3.112 (AB, 2H, JAB =17.5 Hz), 2.088 (s, 3H), 1.962 (m, 2H), 1.416-1.333 (m, 1H), 1.152-1.061 (m, 1H), 0.898-0.726 (m, 7H).

Workup

  1. customPurification
  2. customto provide a solid (0.252 g, 53°-55° C.)

Sources & evidence

ORD record
ord-0b919eee6cd14545bc7a5e2749f9ca2d
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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