Water → HCID 15480786, compound

HRID 842945Notes

Reaction equation

HRID 842945 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[C:6]([CH2:13][C:14]#[N:15])=[CH:5][CH:4]=1.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18].[OH2:22]>C(#N)C>[C:14]([C:13]([C:6]1[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:22])[CH2:18][CH2:17][C:16]([O:20][CH3:21])=[O:19])#[N:15]

Participants

5

Reactant 3

HCID 962WaterHCID 7294Methyl AcrylateHCID 15480785HCID 15480785, compound

Product 1

HCID 15480786HCID 15480786, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Compound 1a (6.2 g, 30 mmol) obtained in Step A in acetonitrile (94 mL) were added a 40% methanolic solution of Triton B (1.4 mL, 3.0 mmol) and methyl acrylate (27 mL, 300 mmol), followed by refluxing for 5 hours. The mixture was allowed to cool, and then poured into water, followed by extraction with ethyl acetate. The organic layer as 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=2/1) to give Compound 1b (6.4 g, 56%) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-0e982db0350d44a38fd61d20f312bd4a
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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