1-Bromohexane → HCID 21954826、化合物

HRID 1011838ノート

反応式

HRID 1011838 の反応式
C([Li])CCC.[C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)#[CH:7].CC(C)([O-])C.[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O.O1CCCC1.CCCCCC>[C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])#[CH:7]

参加物

8

反応物 4

HCID 81011-BromohexaneHCID 1233571-EthynylnaphthaleneHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

生成物 1

HCID 21954826HCID 21954826、化合物収率 47.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-90 °C

実験手順

Under a nitrogen atmosphere at −50° C., 1.6 mol/l hexane solution of n-butyllithium was added to 30 ml of a tetrahydrofuran solution containing 3 g of ethynylnaphthalene. After cooling to −90° C., 15 ml of a tetrahydrofuran solution containing 2.5 g of potassium tertiary butoxide was added thereto, and the mixture was stirred at −80° C. for 1 hour and then allowed to warm to 5° C. 3.3 g of bromohexane was added dropwise at −70° C., and the mixture was stirred at 30° C. overnight. 100 ml of water was added dropwise at 0° C., and the compounds generated were extracted with added hexane. The hexane layer was washed thrice with 300 ml of distilled water and dried over anhydrous magnesium sulfate for 24 hours, and the mixture was then filtered and evaporated for removal of the solvent. After column purification and solvent removal, the product was purified by column chromatography while hexane was used as the developing solvent, to give 2.2 g of 1-ethynyl-2-n-hexylnaphthalene.

後処理

  1. additionwas added
  2. temperatureto warm to 5° C
  3. stirringthe mixture was stirred at 30° C. overnight
  4. extractionthe compounds generated were extracted with added hexane
  5. washThe hexane layer was washed thrice with 300 ml of distilled water
  6. dry with materialdried over anhydrous magnesium sulfate for 24 hours
  7. filtrationthe mixture was then filtered
  8. customevaporated for removal of the solvent
  9. customAfter column purification and solvent removal
  10. customthe product was purified by column chromatography while hexane

出典と根拠

ORDレコード
ord-4b2a3c0c3f4947da864c1ab94e5e9795
出典データセット
uspto-grants-2011_07
特許番号
US07977441B2

反応ノート

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