Acetone Cyanohydrin → HCID 54721753, compound

HRID 357891Notes

Reaction equation

HRID 357891 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) δ 10.850 (bs, 1 H), 7.367-7.287 (m, 5 H), 7.018-7.002 (m, 3 H), 6.724-6.700 (m, 2 H), 3.380 (AB, 2 H, JAB =14 Hz), 3.096 (AB, 2 H, JAB =17 Hz), 1.950-1.820 (m, 2 H), 1.230-1.100 (m, 5 H), 1.080-0.920 (in, 1 H), 0.775 (t, 3 H, J=7 Hz).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-dc7d841e49ef411fa4bb570b20081463
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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