Pyridine → 3-Ethyl-3-(4-iodobenzoyloxymethyl) oxetane

HRID 1491589Notes

Reaction equation

HRID 1491589 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([C:13]1([CH2:17][OH:18])[CH2:16][O:15][CH2:14]1)[CH3:12].N1C=CC=CC=1>CCOCC>[CH2:11]([C:13]1([CH2:17][O:18][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=2)[CH2:16][O:15][CH2:14]1)[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 743734-Iodobenzoyl chlorideHCID 76444Oxt-101

Product 1

HCID 150219453-Ethyl-3-(4-iodobenzoyloxymethyl) oxetane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-iodobenzoyl chloride (11.5 gms) in dry ether (50 ml) was added to a stirred solution of 3-ethyl-3-hydroxymethyloxetane (5 gms) and pyridine (3.5 mls) in ether (100 ml) at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 24 hours. 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 5% ethyl acetate in hexane. 3-Ethyl-3-(4-iodobenzoyloxymethyl) oxetane was obtained as a colourless oil (8.1 gms).

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 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f99e62a8c1214cf49b02a75a2196def9
Source dataset
uspto-grants-1994_12
Patent number
US05371075

Reaction notes

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