Triethylamine → HCID 66643549, compound

HRID 1695422Notes

Reaction equation

HRID 1695422 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[N:8][OH:9])[CH2:3][CH2:2]1.ClN1C(=O)CCC1=O.[C:18]([O:23][CH2:24][CH3:25])(=[O:22])[C:19]#[C:20][CH3:21].C(N(CC)CC)C>CN(C=O)C.C(OC)(C)(C)C>[CH2:24]([O:23][C:18]([C:19]1[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:8][O:9][C:20]=1[CH3:21])=[O:22])[CH3:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 78043Ethyl 2-butynoateHCID 76979141HCID 76979141, compound

Product 1

HCID 66643549HCID 66643549, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of tetrahydro-pyran-4-carbaldehyde oxime (6.5 g, 50 mmol) in DMF (47 mL) was added N-chlorosuccinimide (6.95 g, 50 mmol) at room temperature and the after 3 h the mixture was extracted with tert-butylmethylether (100 mL). The organic extract was then added dropwise over 2 h to a solution of ethyl 2-butynoate (61.2 mL, 52.5 mmol) and triethylamine (8.4 mL, 60 mmol) in tert-butylmethylether (47 mL) heated under reflux and the resulting mixture heated overnight. The reaction mixture was then cooled to room temperature and extracted with tert-butylmethylether and washed with aqueous hydrochloric acid solution (1 N). The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (4.2 g, 35%) as a light yellow solid. MS: m/e=240.2 [M+H]+.

Workup

  1. extractionthe after 3 h the mixture was extracted with tert-butylmethylether (100 mL)
  2. extractionThe organic extract
  3. temperatureheated
  4. temperatureunder reflux
  5. temperaturethe resulting mixture heated overnight
  6. extractionextracted with tert-butylmethylether
  7. washwashed with aqueous hydrochloric acid solution (1 N)
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record
ord-06a33052219a4707bfbb75b6189cd208
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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