Acetone Cyanohydrin → HCID 54721753, compound

HRID 481919Notes

Reaction equation

HRID 481919 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[CH:3]=1.CCN(CC)CC.[C:27](Cl)(=O)[C:28]1[CH:33]=[CH:32][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]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:5][C:4](=[O:19])[C:3]=1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 7412Benzoyl chlorideHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 54687158HCID 54687158, compound

Product 1

HCID 54721753HCID 54721753, 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-n-pentyl-6-phenyl-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), benzoyl chloride (0.13 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 provide an oil (0.215 g). 1H NMR (400 MHz, DMSO-d6) δ10.850 (bs, 1H), 7.367-7.287 (m, 5H), 7.018-7.002 (m, 3H), 6.724-6.700 (m, 2H), 3.380 (AB, 2H, JAB =14 Hz), 3.096 (AB, 2H, JAB =17 Hz), 1.950-1.820 (m, 2H), 1.230-1.100 (m, 5H), 1.080-0.920 (m, 1H), 0.775 (t, 3H, J=7 Hz).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-56c307182011461ebb9a5d99eda4a249
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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