Hydrochloric Acid → HCID 22616353, compound

HRID 842953Notes

Reaction equation

HRID 842953 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C:5]2[C:7]([O:14][CH3:15])=[CH:8][CH:9]=[C:10]([CH2:11][C:12]#[N:13])[C:4]=2[O:3]1.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].[OH2:23].Cl>C(#N)C>[C:12]([C:11]([C:10]1[C:4]2[O:3][C:2]([CH3:16])([CH3:1])[O:6][C:5]=2[C:7]([O:14][CH3:15])=[CH:8][CH:9]=1)([CH2:7][CH2:5][C:4]([O:3][CH3:2])=[O:23])[CH2:19][CH2:18][C:17]([O:21][CH3:22])=[O:20])#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7294Methyl AcrylateHCID 22616363HCID 22616363, compound

Product 1

HCID 22616353HCID 22616353, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Compound 12a (9.0 g, 41 mmol) obtained in Step A in acetonitrile (135 mL) were added a 40% methanolic solution of Triton B (1.9 mL, 4.1 mmol) and methyl acrylate (37 mL , 410 mmol), and the mixture was stirred at room temperature for 30 minutes. Water and 1 mol/L hydrochloric acid were added, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=5/2) to give Compound 12b (11 g, 68%) as a pale yellow oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=5/2)

Sources & evidence

ORD record
ord-1da44471bd0949d1bf129cc04f0337c3
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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