Formaldehyde → HCID 53302309, compound

HRID 899258Notes

Reaction equation

HRID 899258 reaction equation
C(OP([CH:9]([CH2:17][C:18]1[N:19]=[CH:20][S:21][CH:22]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:25]=O>O1CCCC1>[S:21]1[CH:22]=[C:18]([CH2:17][C:9](=[CH2:25])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[N:19]=[CH:20]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 86602109tert-Butyl 2-(diethoxyphosphoryl)-3-(1,3-thiazol-4-yl)propanoate

Product 1

HCID 53302309HCID 53302309, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 2-(diethoxyphosphoryl)-3-(1,3-thiazol-4-yl)propanoate (step 1, 7.17 g, 20.5 mmol) in tetrahydrofuran (100 mL) was added sodiumhydride (60% dispersion in mineral oil, 820 mg, 20.5 mmol) at 0° C. under nitrogen. After 10 min, to the mixture was added paraformaldehyde (1.85 g, 61.5 mmol) and the mixture was stirred at room temperature for 45 min. The mixture was quenched with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3/1) to afford 4.25 g (92%) of the title compound as a colorless oil:

Workup

  1. customThe mixture was quenched with aqueous sodium hydrogen carbonate
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-c396a408a0bf478f9e79ac054b34be8b
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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