Formic Acid → HCID 54180109, compound

HRID 2039426Notes

Reaction equation

HRID 2039426 reaction equation
[OH:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][C:7]#[CH:8])=[O:4].[CH:10](O)=[O:11].CNC1(NC)C=CN=CC1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCCl>[CH:10]([O:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][C:7]#[CH:8])=[O:4])=[O:11]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 10868DicyclohexylcarbodiimideHCID 865890494,4-DimethylaminopyridineHCID 86651912Poly[oxy[(1S)-1-methyl-2-oxo-1,2-ethanediyl]], α-hydro-ω-(2-propyn-1-yloxy)-

Product 1

HCID 54180109HCID 54180109, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

19.96 g (156 mmol) of the obtained 2-propynyl 2-hydroxypropionate, 7.17 g (156 mmol) of formic acid, and 15.23 g (125 mmol) of 4,4-dimethylaminopyridine (nucleating agent) were dissolved in 100 g of 1,2-dichloroethane (solvent), and a mixed solution of 35.35 g (171 mmol) of N,N′-dicyclohexylcarbodiimide (dehydrating agent) and 50 g of 1,2-dichloroethane was added thereto at 10° C., taking 30 minutes. These were reacted at room temperature for 4 hours, and the absence of the starting materials was confirmed through gas chromatography. Subsequently, the reaction liquid was filtered to remove N,N′-dicyclohexylurea, and the filtrate was concentrated. The concentrate was purified through silica gel column chromatography, and from the fraction taken with hexane/ethyl acetate=4/1, 20.78 g (yield 85%) of 2-propynyl 2-(formyloxy)propionate was obtained.

Workup

  1. customThese were reacted at room temperature for 4 hours
  2. customSubsequently, the reaction liquid
  3. filtrationwas filtered
  4. customto remove N,N′-dicyclohexylurea
  5. concentrationthe filtrate was concentrated
  6. customThe concentrate was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-562381b6848f4ce7b99db1c8b213ae7b
Source dataset
uspto-grants-2013_11
Patent number
US08580429B2

Reaction notes

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