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

HRID 357882Notes

Reaction equation

HRID 357882 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) δ 7.376-7.244 (m, 5 H), 6.915 (t, 1 H, J=7.5 Hz), 6.831 (d, 1 H, J=7.5 Hz), 6.549 (d, 1 H, J=7.5 Hz), 6.509 (s, 1 H), 3.369 (AB, 2 H, JAB =14.4 Hz), 3.112 (AB, 2 H, JAB =17.5 Hz), 2.088 (s, 3 H), 1.962 (m, 2 H), 1.416-1.333 (m, 1 H), 1.152-1.061 (m, 1 H), 0.898-0.726 (m, 7 H).

Workup

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

Sources & evidence

ORD record
ord-eba171c9b7bc4fb89265d025d0ff42f0
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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