Acetone Cyanohydrin → HCID 54721668, compound

HRID 1585421Notes

Reaction equation

HRID 1585421 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.[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>[OH:1][C:2]1[CH2:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:5][C:4](=[O:20])[C:3]=1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

9

Reactant 5

HCID 6406Acetone CyanohydrinHCID 7412Benzoyl chlorideHCID 8471Triethylamine2×HCID 5003444Sodium cyanoborohydrideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 54721668HCID 54721668, 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 (0.250 g, 0.940 mmol), Et3N (0.13 mL, 0.94 mmol), benzoyl chloride (0.109 mL, 0.94 mmol), CH2Cl2 (2.0 mL), acetonitrile (5.0 mL), acetone cyanohydrin (0.01 mL, 0.09 mmol), Et3N (0.27 mL, 1.9 mmol), glacial acetic acid (10.0 mL), sodium cyanoborohydride (0.133 g, 2.11 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 (0.105 g, 63-65° C.) 1H NMR (400 MHz, DMSO-d6) δ 11.136 (s, 1 H), 7.501-7.280 (m, 11 H), 6.997-6.932 (m, 2 H), 6.566 (d, 2 H, J=7 Hz), 3.530 (s, 2 H), 3.432 (s, 2 H),

Workup

  1. customPurification
  2. customto provide a solid (0.105 g, 63-65° C.) 1H NMR (400 MHz, DMSO-d6) δ 11.136 (s, 1 H), 7.501-7.280 (m, 11 H), 6.997-6.932 (m, 2 H), 6.566 (d, 2 H, J=7 Hz), 3.530 (s, 2 H), 3.432 (s, 2 H)

Sources & evidence

ORD record
ord-c3432cc357884fe8af88705dfe812e98
Source dataset
uspto-grants-1999_08
Patent number
US05936128

Reaction notes

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