Acetone Cyanohydrin → HCID 54721769, compound

HRID 481912Notes

Reaction equation

HRID 481912 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:14])[C:3]=1[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18].CCN(CC)CC.[CH3:27][C:28]1[CH:36]=CC=C[C:29]=1[C:30](Cl)=O.[CH3:37][C:38](C)(O)[C:39]#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[OH:1][C:2]1[CH2:7][C:6]([CH2:30][CH2:29][CH:28]([CH3:36])[CH3:27])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:5][C:4](=[O:14])[C:3]=1[CH2:15][C:16]1[CH:39]=[CH:38][CH:37]=[CH:18][C:17]=1[CH3:19]

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 702762-Methylbenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 54721774HCID 54721774, compound

Product 1

HCID 54721769HCID 54721769, 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-(3-methylbutyl)-6-phenyl-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 2-methylbenzoyl chloride (0.15 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 (0.51 g, 8.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2Cl2) to provide a solid (0.215 g, 46°-48° C.). 1H NMR (400 MHz, DMSO-d6) δ10.829 (bs, 1H), 7.395-7.303 (m, 5H), 6.994 (d, 1H, J=7 Hz), 6.927 (t, 1H, J=7 Hz), 6.674 (t, 1H, J=7 Hz), 6.149 (d, 1H, J=7 Hz), 3.305 (AB, 2H, JAB =17 Hz), 3.158 (AB, 2H, JAB =17.5 Hz), 2.115 (s, 3H), 1.988-1.854 (m, 2H), 1.439-1.356 (m, 1H), 1.177-1.087 (m, 1H), 0.943-0.852 (m, 1H), 0.792-0.767 (m, 6H).

Workup

  1. customPurification
  2. customto provide a solid (0.215 g, 46°-48° C.)

Sources & evidence

ORD record
ord-eeb8ef1d60744a0992de5882e6ba0670
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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