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

HRID 357889Notes

Reaction equation

HRID 357889 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.[Cl:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=O.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[Cl:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[CH2:31][C:3]1[C:4](=[O:20])[O:5][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)[CH2:7][C:2]=1[OH:1]

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 691102-Chlorobenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 547216893-[(2-Chlorophenyl)methyl]-5,6-dihydro-4-hydroxy-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 (0.17 mL, 1.2 mmol), 2-chlorobenzoyl chloride (0.14 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 (0.50 g, 7.9 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 0.5% MeOH in CH2 Cl2) to provide a solid (0.130 g, 185°-187° C.). 1H NMR (400 MHz, DMSO-d6) δ 11.351 (bs, 1 H), 7.464-7.282 (m, 11 H), 7.054 (t, 1 H, J=7 Hz), 6.679 (td, 1 H, J=1 Hz, J=7.5 Hz), 5.797 (d, 1 H, J=7 Hz), 3.586 (s, 2 H), 3.472 (s, 2 H).

Workup

  1. customPurification
  2. customto provide a solid (0.130 g, 185°-187° C.)

Sources & evidence

ORD record
ord-d72a81f03bb64bf789a3f7824dbc5328
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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