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Acetic Anhydride → (4-Acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester

HRID 238640
ノート
印刷プレビュー

反応式

HRID 238640 の反応式
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([I:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.Cl>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([I:15])=[C:13]([O:16][C:19](=[O:21])[CH3:20])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 7918Acetic AnhydrideHCID 59326608(6-Fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester

生成物 1

HCID 59326600(4-Acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester収率 53.3%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 313Hydrochloric Acid溶媒
HCID 1049
Pyridine
溶媒

実験手順

To a stirred solution of (6-fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester (500 mg, 1.4 mmol) and 4-dimethylaminopyridine (34 mg, 0.28 mmol) in pyridine (3 mL) was added acetic anhydride (160 μL, 1.7 mmol). After being stirred at room temperature overnight, the resulting mixture was diluted with 10% hydrochloric acid (20 mL), and extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with brine (30 mL×2), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column (elution with 20% ethyl acetate in petroleum ether) to afford (4-acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester (300 mg, 53%) as a white solid.

後処理

  1. extractionextracted with ethyl acetate (30 mL×2)
  2. washThe combined organic layers were washed with brine (30 mL×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column (elution with 20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-e7e184dd6ee14ab4acf86753c795b498
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642629B2

反応ノート

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