Acetone Cyanohydrin → HCID 54721769, compound

HRID 357884Notes

Reaction equation

HRID 357884 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) δ 10.829 (bs, 1 H), 7.395-7.303 (m, 5 H), 6.994 (d, 1 H, J=7 Hz), 6.927 (t, 1 H, J=7 Hz), 6.674 (t, 1 H, J =7 Hz), 6.149 (d, 1 H, J=7 Hz), 3.305 (AB, 2 H, JAB =17 Hz), 3.158 (AB, 2 H, JAB =17.5 Hz), 2.115 (s, 3 H), 1.988-1.854 (m, 2 H), 1.439-1.356 (m, 1 H), 1.177-1.087 (m, 1 H), 0.943-0.852 (m, 1 H), 0.792-0.767 (m, 6 H).

Workup

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

Sources & evidence

ORD record
ord-cd3c24ed28d04a44b2d5dc40402f934c
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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