Triphenylphosphine → 3-[4-(2-Methyltetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromide

HRID 741654

反応式

HRID 741654 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][Br:5].[CH3:6][N:7]1[N:11]=[N:10][C:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15](O)=[C:14]([CH3:20])[CH:13]=2)=[N:8]1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.CCOCC>[CH3:6][N:7]1[N:11]=[N:10][C:9]([C:12]2[CH:13]=[C:14]([CH3:20])[C:15]([O:1][CH2:2][CH2:3][CH2:4][Br:5])=[C:16]([CH3:18])[CH:17]=2)=[N:8]1

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 148372Win 58768HCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 153915233-[4-(2-Methyltetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromide収率 82%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of (3-hydroxypropyl)-bromide (2.17 ml, 24 mmol), 4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenol (5.1 g, 25 mmol), and DEAD (4.18 g, 24 mmol)-was dissolved in 50 ml of THF at 0° C. To the above solution was added dropwise triphenylphosphine (6.3 g, 24 mmol) at 0° C. and the mixture was allowed to stir at 0° C. for 0.5 h. The mixture was diluted with 500 ml of water and 100 ml of ether, and the aqueous layere was extracted with ether (2×400 ml). The combined organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was dissolved in 800 ml of ether, and the organic layer was washed with 10% NaOH solution (3×50 ml), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica column chromatography (7 cm column, ethyl acetate/hexane, 1/5) followed by recrystallization from methylene chloride/hexane to afford 6.4 g (82%) of 3-[4-(2-methyltetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromide, as a light yellow oil.

後処理

  1. extractionthe aqueous layere was extracted with ether (2×400 ml)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 800 ml of ether
  5. washthe organic layer was washed with 10% NaOH solution (3×50 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica column chromatography (7 cm column, ethyl acetate/hexane, 1/5)
  9. customfollowed by recrystallization from methylene chloride/hexane

出典と根拠

ORDレコード
ord-3b70ac27b0b04541bf36cbf30af52328
出典データセット
uspto-grants-1996_09
特許番号
US05552420

関連ノート

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