Dimethylformamide → 4-methyl-1,5-octadiyn-4(RS)-ol triethylsilyl ether

HRID 26665

反応式

HRID 26665 の反応式
[CH3:1][C:2]([OH:10])([C:6]#[C:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].[CH2:11]([Si:13](Cl)([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12].CN(C)C=O.C(N(CC)CC)C>O.C1C=CC=CC=1>[CH2:11]([Si:13]([O:10][C:2]([CH3:1])([C:6]#[C:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 213220394-methyl-1,5-octadiyn-4(RS)-ol

生成物 1

HCID 213220414-methyl-1,5-octadiyn-4(RS)-ol triethylsilyl ether

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

A mixture consisting of 1.25 parts of 4-methyl-1,5-octadiyn-4(RS)-ol, 1.5 parts of triethylsilyl chloride, 2.5 parts by volume of dimethylformamide and 1 part by volume of triethylamine was stirred in an atmosphere of nitrogen at room temperature for about 24 hours. The mixture was then poured into benzene and diluted with water. The layers were separated and the organic layer was washed successively with dilute hydrochloric acid, water and saturated aqueous potassium bicarbonate, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. Adsorption of the residue on a silica gel chromatographic column followed by elution with hexane afforded 4-methyl-1,5-octadiyn-4(RS)-ol triethylsilyl ether.

後処理

  1. customThe layers were separated
  2. washthe organic layer was washed successively with dilute hydrochloric acid, water and saturated aqueous potassium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. washAdsorption of the residue on a silica gel chromatographic column followed by elution with hexane

出典と根拠

ORDレコード
ord-689e2f5deb7742b2b55bcd01eb67d1b2
出典データセット
uspto-grants-1979_04
特許番号
US04151187

関連ノート

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