Acetone Cyanohydrin → HCID 54721651, compound

HRID 1585426Notes

Reaction equation

HRID 1585426 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), 1-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 CH2Cl2) 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-89469cf886744dff9b86655c3f3fddbb
Source dataset
uspto-grants-1999_08
Patent number
US05936128

Reaction notes

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