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

HRID 26665

반응식

HRID 26665 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-689e2f5deb7742b2b55bcd01eb67d1b2
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04151187

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