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Sodium hydride → 1-(tert-Butyldimethylsilyloxymethyl)-4-(13-allyloxy-2,5,8,11-tetraoxa-tridecyl)-benzene

HRID 1714714
ノート
印刷プレビュー

反応式

HRID 1714714 の反応式
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16])[CH:2]=[CH2:3].[H-].[Na+].[Si:19]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34]I)=[CH:30][CH:29]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C1COCC1>[Si:19]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:1][CH:2]=[CH2:3])=[CH:30][CH:29]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]
参加物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 24758Sodium hydrideHCID 101252143,6,9,12-Tetraoxapentadec-14-en-1-olHCID 107373351-[(tert-Butyldimethylsilyl)oxymethyl]-4-iodomethylbenzene

生成物 1

HCID 686386381-(tert-Butyldimethylsilyloxymethyl)-4-(13-allyloxy-2,5,8,11-tetraoxa-tridecyl)-benzene収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 11-allyloxy-3,6,9-trioxaundecanol (83, 2.33 g, 9.94 mmol) in dry THF (40 mL), sodium hydride (0.95 g, 39.8 mmol) is added in several portions under an argon atmosphere. The mixture is stirred for 30 min. A solution of the iodo derivative 45 (3.0 g, 8.28 mmol) in dry THF (10 mL) is added dropwise, and the mixture stirred for 15 h. The reaction is quenched by adding 2 mL of water, and 70% of the amount of THF is evaporated in vacuo. To dilute the mixture, 70 mL of water are added, and the solution extracted with 5 times 50 mL ethyl acetate. The combined organic extracts are dried over MgSO4 and concentrated in vacuo. The yellow oil obtained is purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1) to give the title product 84 as a pale yellow oil (1.96 g, 4.2 mmol, 51%).

後処理

  1. stirringthe mixture stirred for 15 h
  2. customThe reaction is quenched
  3. additionby adding 2 mL of water, and 70% of the amount of THF
  4. customis evaporated in vacuo
  5. additionTo dilute the mixture, 70 mL of water
  6. additionare added
  7. extractionthe solution extracted with 5 times 50 mL ethyl acetate
  8. dry with materialThe combined organic extracts are dried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe yellow oil obtained
  11. customis purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1)

出典と根拠

ORDレコード
ord-05c0fca5058b4520a8617efc7f70a631
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07799524B2

反応ノート

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