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

HRID 466512

Reaction equation

HRID 466512 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 (preeluted 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 (preeluted with 1% triethylamine in hexane)
  5. washeluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c0cd025686834317935ac4c1969a3a2f
Source dataset
uspto-grants-1992_10
Patent number
US05157029

Linked notes

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