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

HRID 1585422Notes

Reaction equation

HRID 1585422 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.[CH3:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](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]([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)[O:5][C:4](=[O:20])[C:3]=1[CH2:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:31]([CH3:32])[CH:30]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 743753-Methylbenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 547217805,6-Dihydro-4-hydroxy-3-[(3-methylphenyl)methyl]-6,6-diphenyl-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-6,6-diphenyl-2H-pyran-2-one (0.300 g, 1.13 mmol), Et3N (0.16 mL, 1.15 mmol), 3-methylbenzoyl chloride (0.15 mL, 1.13 mmol), CH2Cl2 (4.0 mL), acetonitrile (4.0 mL), acetone cyanohydrin (0.05 mL, 0.58 mmol), Et3N (0.32 mL, 2.3 mmol), glacial acetic acid (4.0 mL), sodium cyanoborohydride (0.28 g, 4.5 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2Cl2) to provide a solid (0.223 g, m.p. 57-59° C.). 1H NMR (400 MHz, DMSO-d6) δ 11.112 (bs, 1 H), 7.414-7.270 (m, 10 H), 6.875-6.812 (m, 2 H), 6.429-6.392 (m, 2 H), 3.527 (s, 2 H), 3.409 (s, 2 H), 2.060 (s, 3 H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-0b5925da70404629928bdb5a056e1fc9
Source dataset
uspto-grants-1999_08
Patent number
US05936128

Reaction notes

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