Pyridine → HCID 23042579, compound

HRID 2165868Notes

Reaction equation

HRID 2165868 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[OH:11][CH:12]([C:14]1([CH2:18][CH2:19][CH3:20])[CH2:17][O:16][CH2:15]1)[CH3:13].N1C=CC=CC=1>CCOCC>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:11][CH:12]([C:14]2([CH2:18][CH2:19][CH3:20])[CH2:17][O:16][CH2:15]2)[CH3:13])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 743734-Iodobenzoyl chlorideHCID 23042576HCID 23042576, compound

Product 1

HCID 23042579HCID 23042579, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-iodobenzoyl chloride (3.5 g) in dry ether (25 ml) was added to a stirred solution of 3-(1-hydroxyethyl)-3-n-propyloxetane (1.7 g) and pyridine (1.8 ml) in ether (50 ml) at 0° C. The resulting mixture was stirred for 24 hours at room temperature. After this time the mixture was washed with water and brine. The organic extracts were dried over anhydrous magnesium sulphate and then evaporated in vacuo. The residue was purified by column chromatography on silica (pre-eluted with 1% triethylamine in hexane) and eluted with hexane/ether mixtures. 3-[1-(4-Iodobenzoyloxy)ethyl]-3-n-propyloxetane was obtained as a colourless oil (1.8 g).

Workup

  1. washAfter this time the mixture was washed with water and brine
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulphate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica (pre-eluted with 1% triethylamine in hexane)
  5. washeluted with hexane/ether mixtures

Sources & evidence

ORD record
ord-44a50545973b4bb2a9c8556be2923c8b
Source dataset
uspto-grants-1990_07
Patent number
US04942173

Reaction notes

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