Acetone Cyanohydrin → HCID 54721651, compound

HRID 357886Notes

Reaction equation

HRID 357886 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.[C:28]1([C:38](Cl)=O)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[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]([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[CH2:38][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 701461-Naphthalenecarbonyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 54721651HCID 54721651, compound

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 (0.160 mL, 1.15 mmol), l-naphthoyl chloride (1.13 mmol), CH2Cl2 (6.0 mL), acetonitrile (4.0 mL), acetone cyanohydrin (0.05 mL, 0.5 mmol), Et3N (0.35 mL, 2.5 mmol), glacial acetic acid (6.0 mL), sodium cyanoborohydride (0.50 g, 7.9 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1.5% MeOH in CH2 Cl2) to provide a solid (0.120 g, 203°-205° C.(dec.)). 1H NMR (400 MHz, DMSO-d6) δ 11.223 (bs, 1 H), 8.057 (d, 1 H, J=7 Hz), 7.855-7.821 (m, 1 H), 7.603 (d, 1 H, J=8 Hz), 7.514-7.302 (m, 12 H), 6.866 (dd, 1 H, J=6.5 Hz, J=8 Hz), 5.975 (d, 1 H, J=7 Hz), 3.874 (s, 2 H), 3.621 (s, 2 H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-dd8e95e2dffc47059bd30680bbbaa680
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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