Water → HCID 178470994, compound

HRID 243709Notes

Reaction equation

HRID 243709 reaction equation
[CH3:1][CH:2]([C:8](=O)[CH2:9][C:10](=O)[CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].O.[NH2:15][NH2:16]>C1COCC1>[CH3:11][C:10]1[CH:9]=[C:8]([CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[NH:16][N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 12209136HCID 12209136, compound

Product 1

HCID 178470994HCID 178470994, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 18.6 g (100 mmol) of ethyl 2-methyl-3,5-dioxohexanoate from step A above in 200 mL of THF and 50 mL of water was added 3.45 mL (110 mmol) of anhydrous hydrazine. The biphasic reaction mixture was stirred at ambient temperature overnight then evaporated to dryness in vacuo. The crude yellow residue was dissolved in an ethyl acetate and water mixture and flushed through a 50 g silica gel plug. The filtrate was then evaporated to dryness in vacuo and the residue purified by silica gel chromatography eluting with a 0-100% ethyl acetate in hexanes gradient to afford the title compound as a yellow oil (1.89 g, 10%). 1H NMR (CDCl3, 500 MHz) δ 7.26 (s, 1H), 5.98 (s, 1H), 4.20-4.12 (m, 2H), 3.81 (q, J=7.3 Hz, 1H), 2.28 (s, 3H), 1.51 (d, J=7.3 Hz, 3H), 1.25 (t, J=7.1 Hz, 3H). LC-MS: m/z (ES) 183 (MH)+.

Workup

  1. customThe biphasic reaction mixture
  2. customthen evaporated to dryness in vacuo
  3. dissolutionThe crude yellow residue was dissolved in an ethyl acetate and water mixture
  4. customflushed through a 50 g silica gel plug
  5. customThe filtrate was then evaporated to dryness in vacuo
  6. customthe residue purified by silica gel chromatography
  7. washeluting with a 0-100% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-4619d5ec6e134e01906bdf200aea3640
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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