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Water → 2-[3-(2-Dimethylaminoethoxy)propyl]-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2308881
ノート
印刷プレビュー

反応式

HRID 2308881 の反応式
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].I[CH2:10][CH2:11][CH2:12][CH:13]1[S:17][C:16]2[C:18]([CH3:28])=[C:19]([O:24][CH2:25][O:26][CH3:27])[C:20]([CH3:23])=[C:21]([CH3:22])[C:15]=2[O:14]1.O>CN(C)C=O>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][CH2:10][CH2:11][CH2:12][CH:13]1[S:17][C:16]2[C:18]([CH3:28])=[C:19]([O:24][CH2:25][O:26][CH3:27])[C:20]([CH3:23])=[C:21]([CH3:22])[C:15]=2[O:14]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 148021922-(3-Iodopropyl)-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole

生成物 1

HCID 148021942-[3-(2-Dimethylaminoethoxy)propyl]-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

反応条件

温度
50 °C

実験手順

210 mg of 2-dimethylaminoethanol were dissolved in 3 ml of dimethylformamide, and then 100 mg of a 50% w/w oily suspension of sodium hydride were added to the solution. This reaction mixture was then heated for 1 hour at 50° C. The reaction mixture was then cooled with ice, and a solution of 900 mg of 2-(3-iodopropyl)-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 86) in 2 ml of dimethylformamide was added dropwise, while stirring. After completion of the dropwise addition, the temperature of the reaction mixture was gradually raised, and then the mixture was heated for a further 2 hours at 50° C. The reaction mixture was then poured into water, and the resulting precipitate was extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate. The benzene was distilled off under reduced pressure. The residual crude oily reaction product was separated by silica gel column chromatography. The fraction eluted with benzene was removed, while the fraction eluted with a 20:1 by volume mixture of ethyl acetate and triethylamine was subjected to silica gel Lobar column chromatography, eluted with the same eluent, to give the title compound.

後処理

  1. additionwere added to the solution
  2. temperatureThe reaction mixture was then cooled with ice
  3. additionAfter completion of the dropwise addition
  4. temperaturethe temperature of the reaction mixture was gradually raised
  5. temperaturethe mixture was heated for a further 2 hours at 50° C
  6. extractionthe resulting precipitate was extracted with benzene
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe benzene was distilled off under reduced pressure
  10. customThe residual crude oily reaction product was separated by silica gel column chromatography
  11. washThe fraction eluted with benzene
  12. customwas removed, while the fraction
  13. washeluted with a 20:1 by volume mixture of ethyl acetate and triethylamine
  14. washeluted with the same eluent

出典と根拠

ORDレコード
ord-acfd9d98790e4f26bbd2de9917dbe307
出典データセット
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04691027

反応ノート

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