Acetone Cyanohydrin → HCID 54721563, compound

HRID 357892Notes

Reaction equation

HRID 357892 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:20])[CH:3]=1.CCN(CC)CC.[Cl:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=O.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[Cl:28][CH2:29][C:30]1[CH:31]=[C:32]([CH2:33][C:3]2[C:4](=[O:20])[O:5][C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:7][C:2]=2[OH:1])[CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 27333243-(Chloromethyl)benzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 54721563HCID 54721563, 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-6,6-diphenyl-2H-pyran-2-one (0.300 g, 1.13 mmol), Et3N (0.17 mL, 1.2 mmol), 3-(chloromethyl)benzoyl chloride (0.13 mL, 1.13 mmol), CH2Cl2 (5.0 mL), acetonitrile (5.0 mL), acetone cyanohydrin (0.05 mL, 0.5 mmol), Et3N (0.35 mL, 2.5 mmol), glacial acetic acid (6.0 mL), sodium cyanoborohydride (0.50 g, 7.9 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 4/1 hexane/ethyl acetate to 3/2 hexane/ethyl acetate) to provide a solid (0.118 g, 135°-137° .C). 1H NMR (400 MHz, DMSO-d6) δ 11.211 (s, 1 H), 7.418-7.280 (m, 10 H), 7.088 (d, 1 H, 7.5 Hz), 6.975 (t, 1 H, J=7.5 Hz), 6.689 (s, 1 H), 6.513 (d, 1 H, J=7.5 Hz), 4.498 (s, 2 H), 3.540 (s, 2 H), 3.447 (s, 2 H).

Workup

  1. customPurification
  2. customto provide a solid (0.118 g, 135°-137° .C)

Sources & evidence

ORD record
ord-0baaeb94cf2f44cebe2a546643211241
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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