Acetophenone → HCID 67384503, compound

HRID 1471913Notes

Reaction equation

HRID 1471913 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:20]1([C:23](Cl)=O)[CH2:22][CH2:21]1.O.[NH2:27][NH2:28]>C1(C)C=CC=CC=1.CCO.CC(O)=O>[CH:20]1([C:23]2[NH:28][N:27]=[C:1]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:2]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 7410AcetophenoneHCID 24654Hydrazine hydrate (1:1)HCID 77637Cyclopropanecarbonyl chlorideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 67384503HCID 67384503, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of acetophenone (5.0 g, 41.6 mmol) in dry toluene (5 mL) was added LiHMDS (42.0 mL, 1.0 M in THF, 42.0 mmol) via syringe at 0° C. under argon. After 5 min, cyclopropanecarbonyl chloride (4.35 g, 41.6 mmol) was added in one portion via syringe. The ice bath was removed and AcOH (2 mL), EtOH (50 mL), and hydrazine hydrate (10 mL, 64% aq., 127.8 mmol) was added. The mixture was refluxed for 30 min, cooled to room temperature, and concentrated. The residue was extracted with EtOAc, washed with brine, dried over MgSO4, and purified by silica gel column chromatography to give the title compound as colorless oil (4.5 g). LCMS m/z=184.7 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.71-0.80 (m, 2H), 0.89-1.00 (m, 2H), 1.81-1.98 (m, 1H), 6.22 (s, 1H), 7.11-7.56 (m, 5H), 10.50 (bs, 1H).

Workup

  1. customThe ice bath was removed
  2. temperatureThe mixture was refluxed for 30 min
  3. concentrationconcentrated
  4. extractionThe residue was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-f4322afcadb34fc2988d7c38f5843ab4
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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