Acetone Cyanohydrin → HCID 54721744, compound

HRID 357890Notes

Reaction equation

HRID 357890 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) δ 10.849 (bs, 1 H), 7.371-7.284 (m, 5 H), 7.040-7.004 (m, 3 H), 6.747-6.724 (m, 2 H), 3.395 (s, 2 H), 3.117 (AB, 2 H, JAB=17.5 Hz), 2.059-1.950 (m, 2 H), 1.652-1.578 (m, 2 H), 1.561-1.289 (m, 5 H), 1.021-0.844 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-38a5ebdd1a8d4c2ba9b15d0f3a5fca95
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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