Water → (3-Methyloxetan-3-yl)methyl hex-5-ynoate

HRID 1294756Notes

Reaction equation

HRID 1294756 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[CH3:9][C:10]1([CH2:14]O)[CH2:13][O:12][CH2:11]1.Cl.C(N=C=NCCCN(C)C)C.O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:9][C:10]1([CH2:14][O:7][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6])[CH2:13][O:12][CH2:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 1378373-Methyl-3-oxetanemethanolHCID 1430365-Hexynoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 13123201(3-Methyloxetan-3-yl)methyl hex-5-ynoateYield 95.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-hexynoic acid (10.0 g) and 3-methyl-3-oxetane methanol (10.0 g) in methylene chloride (50 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (20.5 g), and 4-dimethylaminopyridine (1.09 g) were added under cooling with ice. The mixture was stirred at room temperature for 45 minutes. The reaction mixture was poured into iced water and extracted with ethyl acetate. The orgnic layer was washed by water and an aqueous saturated solution of sodium chloride, sucessively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified with silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the title compound (16.7 g) having the following physical data.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe orgnic layer was washed by water
  4. dry with materialan aqueous saturated solution of sodium chloride, sucessively, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-43dd6aefd31f42dbab4975f80a866fda
Source dataset
uspto-grants-2007_07
Patent number
US07241784B2

Reaction notes

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