Acetone Cyanohydrin → HCID 19898205, compound

HRID 1196411Notes

Reaction equation

HRID 1196411 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:24][CH:25]1[O:30][C:29](=[O:31])[CH2:28][C:27](=[O:32])[CH2:26]1.CC(C)(O)C#N>C(#N)C.ClCCl>[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([CH:28]1[C:27](=[O:32])[CH2:26][CH:25]([CH3:24])[O:30][C:29]1=[O:31])=[O:7])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 130878746-Methyloxane-2,4-dioneHCID 143235242-Nitro-4-(trifluoromethyl)benzoyl chloride

Product 1

HCID 19898205HCID 19898205, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

2-Nitro-4-trifluoromethylbenzoyl chloride (4 g) was added at 0°-5° C. to a stirred solution of triethylamine (2.2 ml) and 6-methyltetrahydropyran-2,4-dione (2 g) in dry acetonitrile (25 ml) and the mixture was stirred at ambient temperature for 4 hours. Triethylamine (6.4 ml) and acetone cyanohydrin (0.3 ml) were added successively to the solution and the mixture stirred at ambient temperature for a further 2 hours. The mixture was diluted with dichloromethane (50 ml) and washed successively with 2N hydrochloric acid (20 ml) and water (3×20 ml). The dichloromethane solution was dried over sodium sulphate and evaporated under reduced pressure to give a brown gum which was triturated with a mixture of chloroform and hexane (1:1, 20 ml) to give 3-(2-nitro-4-trifluoromethylbenzoyl)-6-methyltetrahydropyran-2,4-dione (2.2 g), mp 135°-136.5° C., as a light cream crystalline solid.

Workup

  1. stirringthe mixture stirred at ambient temperature for a further 2 hours
  2. washwashed successively with 2N hydrochloric acid (20 ml) and water (3×20 ml)
  3. dry with materialThe dichloromethane solution was dried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customto give a brown gum which
  6. customwas triturated with a mixture of chloroform and hexane (1:1, 20 ml)

Sources & evidence

ORD record
ord-59c2d9386778469a9cc894cea3abe2bd
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

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