Acetone Cyanohydrin → HCID 54721744, compound

HRID 481918Notes

Reaction equation

HRID 481918 reaction equation
[CH:1]1([CH2:6][C:7]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:11](=[O:13])[CH:10]=[C:9]([OH:14])[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[C:28](Cl)(=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[CH:1]1([CH2:6][C:7]2([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:12][C:11](=[O:13])[C:10]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:9]([OH:14])[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 7412Benzoyl chlorideHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 54690707HCID 54690707, compound

Product 1

HCID 54721744HCID 54721744, 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: 6-cyclopentylmethyl-5,6-dihydro-4-hydroxy-6-phenyl-2H-pyran-2-one (0.300 g, 1.10 mmol), Et3N (0.17 mL, 1.2 mmol), benzoyl chloride (0.13 mL, 1.10 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 a solid (0.188 g, 53°-55° C.). 1H NMR (400 MHz, DMSO-d6) δ10.849 (bs, 1H), 7.371-7.284 (m, 5H), 7.040-7.004 (m, 3H), 6.747-6.724 (m, 2H), 3.395 (s, 2H), 3.117 (AB, 2H, JAB=17.5 Hz), 2.059-1.950 (m, 2H), 1.652-1.578 (m, 2H), 1.561-1.289 (m, 5H), 1.021-0.844 (m, 2H).

Workup

  1. customPurification
  2. customto provide a solid (0.188 g, 53°-55° C.)

Sources & evidence

ORD record
ord-66d7408d7477466f8c507aafca67ab6a
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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