Acetone Cyanohydrin → HCID 178519060, compound

HRID 1585428Notes

Reaction equation

HRID 1585428 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.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(CC)CC.C[C:38](C)([OH:41])C#N>C(OCC)C.ClCCl>[C:21]([C:38]([C:3]1[C:4](=[O:20])[O:5][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)[CH2:7][C:2]=1[OH:1])=[O:41])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

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

Product 1

HCID 178519060HCID 178519060, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

The desired compounds were prepared by adding 5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (0.500 g, 1.88 mmol) and dry dichloromethane (10.0 mL) to a reaction vessel followed by the addition of the benzoyl chloride (0.22 mL, 1.88 mmol) and Et3N (0.28 mL, 2.0 mmol). The mixture was allowed to stir for 15 min. and then diluted with diethyl ether. The mixture was then washed with sat'd NaHCO3 (2×) and the organic layer dried with MgSO4. The solvent was then removed in vacuo, the residue redissolved in CH3CN and then treated with Et3N (0.56 mL, 4.0 mmol) and acetone cyanohydrin. The mixture was allowed to stir for 18 h and then diluted with diethyl ether. The mixture was then washed with 1.0 N HCl, dried with NaSO4, and the solvent removed in vacuo. Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 3/2 hexane/ethyl acetate) to provide a solid (0.357 g, 66-68° C.). 1H NMR (400 MHz, CDCl3) δ 7.495-7.208 (m, 15 H), 3.558 (s, 2 H).

Workup

  1. washThe mixture was then washed with sat'd NaHCO3 (2×)
  2. dry with materialthe organic layer dried with MgSO4
  3. customThe solvent was then removed in vacuo
  4. dissolutionthe residue redissolved in CH3CN
  5. stirringto stir for 18 h
  6. washThe mixture was then washed with 1.0 N HCl
  7. dry with materialdried with NaSO4
  8. customthe solvent removed in vacuo
  9. customPurification
  10. customto provide a solid (0.357 g, 66-68° C.)

Sources & evidence

ORD record
ord-0c5603438c7a4d7883d22fa63c318546
Source dataset
uspto-grants-1999_08
Patent number
US05936128

Reaction notes

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