Sodium Iodide → 4-(2-Iodoethyl)-2-methoxyphenyl acetate

HRID 1805930

反応式

HRID 1805930 の反応式
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:7][C:6]=1[O:24][CH3:25])(=[O:3])[CH3:2].C(OC1C=CC(CCO)=CC=1OC)(=O)C.[I-:41].[Na+]>CC(C)=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][I:41])=[CH:7][C:6]=1[O:24][CH3:25])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 673766674-(2-Hydroxyethyl)-2-methoxyphenyl acetateHCID 866573972-Methoxy-4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl acetate

生成物 1

HCID 673761204-(2-Iodoethyl)-2-methoxyphenyl acetate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A 6:4 mixture of 2-methoxy-4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl acetate and 4-(2-hydroxyethyl)-2-methoxyphenyl acetate (1.57 g, 4.31 mmol) and sodium iodide (0.706 mL, 17.2 mmol) in dry acetone (28 mL) was stirred at room temperature overnight with protection from light. The acetone was removed in vacuo and the residue was triturated with toluene and filtered through a plug of Celite to remove insoluble inorganic material. The filtrate was concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 50% EtOAc in hexanes over 4536 mL) to give 4-(2-iodoethyl)-2-methoxyphenyl acetate. Rf=0.58 (20% EtOAc/hexanes). LCMS calc.=321.0; found=320.7 (M+H)+.

後処理

  1. customThe acetone was removed in vacuo
  2. customthe residue was triturated with toluene
  3. filtrationfiltered through a plug of Celite
  4. customto remove insoluble inorganic material
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford the crude product
  7. customThis was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 50% EtOAc in hexanes over 4536 mL)

出典と根拠

ORDレコード
ord-e201b553fde2457e90777b21847e7833
出典データセット
uspto-grants-2013_01
特許番号
US08354454B2

関連ノート

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