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Stannane, chlorotricyclohexyl- → Tricyclohexyl [o-(1-hydroxyethyl)phenyl]tin

HRID 376825
ノート
印刷プレビュー

反応式

HRID 376825 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:10])[CH3:9].C([Li])CCC.[CH:16]1([Sn:22](Cl)([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>O.C(OCC)C.CCCCCC>[CH:29]1([Sn:22]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH:8]([OH:10])[CH3:9])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]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

7

反応物 3

HCID 76539Stannane, chlorotricyclohexyl-HCID 954551-(2-Bromophenyl)ethanolHCID 178418339Butyllithium

生成物 1

HCID 19359512Tricyclohexyl [o-(1-hydroxyethyl)phenyl]tin収率 73%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether
溶媒
2 回
HCID 8058Hexane溶媒2 回

反応条件

温度
-30 °C

実験手順

10.1 g of o-bromo-1-phenylethanol (50.2 mmol) and 50 ml of diethylether were mixed together in a 500 ml two-neck flask, which was equipped with a stirrer and isobaric dropping funnel. To this mixture, 64.5 ml of hexane solution of n-butyl lithium was gradually added dropwise at -78° C. Subsequently, the temperature was raised to -30° C., and the mixture was stirred for 1 hour while maintaining the same temperature. The reaction mixture was cooled back to -78° C., and a mixed solvent solution containing 20.2 g of tricyclohexyltin chloride (50.1 mmol), 100 ml of hexane, and 50 ml of diethylether was added dropwise thereto. The temperature was raised back to -30° C., and the mixture was stirred for 12 hours at the same temperature. Upon completion of the reaction, 100 ml of water was added, and the organic substance was extracted three times, with 200 ml of diethylether for each. After the solvent was removed under reduced pressure, the oily product was purified by column chromatography on silica gel (for which, 50 g of silica gel, and a mixed solvent of hexane and diethylether, as a developing solvent, were employed) to yield 17.9 g of the final product (yield=73.0%).

後処理

  1. customwhich was equipped with a stirrer
  2. temperaturewhile maintaining the same temperature
  3. temperatureThe reaction mixture was cooled back to -78° C.
  4. additionwas added dropwise
  5. temperatureThe temperature was raised back to -30° C.
  6. stirringthe mixture was stirred for 12 hours at the same temperature
  7. additionwas added
  8. extractionthe organic substance was extracted three times
  9. customAfter the solvent was removed under reduced pressure
  10. customthe oily product was purified by column chromatography on silica gel (for which, 50 g of silica gel

出典と根拠

ORDレコード
ord-dc7c027c1dee4fd7a5af4337fbe8a0f9
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06022822

反応ノート

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