ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Water → 2-[3-[3-(1-Adamantyl)-4-tert.butyldimethylsilyloxyphenyl]-allyl]-1,3-dioxane

HRID 893425
ノート
印刷プレビュー

反応式

HRID 893425 の反応式
[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:29]12([C:39]3[C:40]([O:51][SiH:52]([CH3:54])[CH3:53])=[C:41]([CH:44]=[CH:45][C:46]=3[C:47]([CH3:50])([CH3:49])[CH3:48])[CH:42]=O)[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2.O>C1COCC1>[C:29]12([C:39]3[C:40]([O:51][SiH:52]([CH3:54])[CH3:53])=[C:41]([CH:42]=[CH:9][CH2:8][CH:3]4[O:2][CH2:7][CH2:6][CH2:5][O:4]4)[CH:44]=[CH:45][C:46]=3[C:47]([CH3:50])([CH3:48])[CH3:49])[CH2:30][CH:31]3[CH2:37][CH:35]([CH2:34][CH:33]([CH2:32]3)[CH2:38]1)[CH2:36]2
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

5

反応物 3

HCID 962WaterHCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 1373291173(1-Adamantyl)-4-tert.butyl-dimethylsilyloxybenzaldehyde

生成物 1

HCID 1373285792-[3-[3-(1-Adamantyl)-4-tert.butyldimethylsilyloxyphenyl]-allyl]-1,3-dioxane収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

33 g (72.1 mmoles) of [2-(1,3-dioxan-2-yl)ethyl] triphenylphosphonium bromide are suspended in 100 ml of THF. The suspension is cooled to 0° C. and 8.5 g (75.6 mmoles) of potassium terbutylate are added in small amounts. The mixture is left to stand until its temperature reaches 20° C. It is then stirred for 1 hour at which point it is cooled to 0° C. There is then slowly added a solution of 3-(1-adamantyl)-4-tert.butyl-dimethylsilyloxybenzaldehyde in 100 ml of TMF. Once the addition has ended, the mixture is left to stand until its temperature reaches ambient temperature at which point it is stirred for 2 hours, then poured into water, and extracted with methylene chloride. The organic phase is decanted, washed with water, dried over MgSO4 and the solvents evaporated. The residue is purified by passage through a silica column (eluant: 50:50 mixture of CH2Cl2 and hexane), yielding 19.4 g (95% yield) of the expected mixture containing more than 90% of isomer Z, and less than 10% of isomer E.

後処理

  1. waitThe mixture is left
  2. customreaches 20° C
  3. temperatureis cooled to 0° C
  4. additionOnce the addition
  5. waitthe mixture is left
  6. customreaches ambient temperature at which point it
  7. stirringis stirred for 2 hours
  8. extractionextracted with methylene chloride
  9. customThe organic phase is decanted
  10. washwashed with water
  11. dry with materialdried over MgSO4
  12. customthe solvents evaporated
  13. customThe residue is purified by passage through a silica column (eluant: 50:50 mixture of CH2Cl2 and hexane)

出典と根拠

ORDレコード
ord-a95d43c720c2406fabee5ca1808a4a68
出典データセット
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05124473

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート