(+-)-2-Butanol → HCID 22664389, compound

HRID 392558Notes

Reaction equation

HRID 392558 reaction equation
[OH-].[Na+].CC(O)CC.[F:8][C:9]([F:46])([F:45])[C:10]1[CH:44]=[CH:43][C:13]2=[N+:14]([O-])[N:15]([C:17]3[CH:22]=[C:21]([C:23]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:31]([C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)([CH3:33])[CH3:32])[C:18]=3[OH:41])[N:16]=[C:12]2[CH:11]=1.ClC1C(=O)C2C(C(=O)C=1Cl)=CC=CC=2>C(C(C)=O)C>[F:46][C:9]([F:8])([F:45])[C:10]1[CH:44]=[CH:43][C:13]2=[N:14][N:15]([C:17]3[CH:22]=[C:21]([C:23]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:24])[CH3:25])[CH:20]=[C:19]([C:31]([C:34]4[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=4)([CH3:33])[CH3:32])[C:18]=3[OH:41])[N:16]=[C:12]2[CH:11]=1

Participants

6

Reactant 4

HCID 6568(+-)-2-ButanolHCID 8342DichloneHCID 14798Sodium HydroxideHCID 69920027HCID 69920027, compound

Product 1

HCID 22664389HCID 22664389, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
83 °C

Procedure

To a 500 mL three-necked flask equipped with a mechanical stirrer, 3.7 g of sodium hydroxide pellets and 50 mL of 2-butanol are charged and heated to 83° C. To this solution is added over a 90-minute period a solution of 230 mL of methyl ethyl ketone, 20 g of the benzo-triazole-N-oxide prepared in Example 15 and 0.85 g of 2,3-dichloro-1,4-naphthoquinone. The mixture is refluxed at 88° C. for one hour while distilling off methyl ethyl ketone. After cooling down to ambient temperature, 25 g of water and 30 mL of ethyl acetate are added at which time the pH is reduced to 3 with 30% aqueous sulfuric acid. After splitting off the aqueous layer, the solvent is removed by distillation. The crude solid is purified by silica gel chromatography using heptane/ethyl acetate (49/1) as eluent. After collecting the desired fractions and crystallizing from methanol/toluene, the title compound is obtained in a yield of 14 g as a light yellow solid melting at 120-122° C. The structure is consistent with analyses by 1Hnmr, 19Fnmr and mass spectroscopy.

Workup

  1. customTo a 500 mL three-necked flask equipped with a mechanical stirrer
  2. temperatureThe mixture is refluxed at 88° C. for one hour
  3. distillationwhile distilling off methyl ethyl ketone
  4. temperatureAfter cooling down to ambient temperature
  5. addition25 g of water and 30 mL of ethyl acetate are added at which time the pH
  6. customthe solvent is removed by distillation
  7. customThe crude solid is purified by silica gel chromatography
  8. customAfter collecting the desired fractions
  9. customcrystallizing from methanol/toluene

Sources & evidence

ORD record
ord-2f1e6a03502c402da95bad0279497ca3
Source dataset
uspto-grants-2004_10
Patent number
US06800676B2

Reaction notes

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