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Toluene → HCID 22841014、化合物

HRID 329514
ノート
印刷プレビュー

反応式

HRID 329514 の反応式
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([OH:16])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[OH-].[K+].C1(C)C=CC=CC=1>O>[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([O:16][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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 1140TolueneHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 22841016HCID 22841016、化合物

生成物 1

HCID 22841014HCID 22841014、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1.037 g of dl-cis-2-benzyloxymethyltetrahydropyran-3-ol (prepared as described in Preparation 33), 1.709 g of hexadecyl bromide, 0.77 g of potassium hydroxide and 15 ml of toluene was heated, with stirring, at 120° C. for 10 hours. At the end of this time, the reaction mixture was cooled and then poured into water. The aqueous layer was extracted twice with diethyl ether. The organic layer and the extracts were combined, washed with water, dried over anhydrous magnesium sulfate and condensed by evaporation under reduced pressure. The resulting oily residue (3.3 g) was subjected to column chromatography through 50 g of silica gel. The fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane gave 1.455 g of the title compound as a colorless oily substance.

後処理

  1. temperaturewas heated
  2. temperatureAt the end of this time, the reaction mixture was cooled
  3. extractionThe aqueous layer was extracted twice with diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate and condensed by evaporation under reduced pressure
  6. washThe fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane

出典と根拠

ORDレコード
ord-f727afdebb8241899a9b99fb021713ec
出典データセット
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04891363

反応ノート

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