Hexane → 1-Phenyl-8-(2-tetrahydropyranyloxy)-1-octyne

HRID 477007

反応式

HRID 477007 の反応式
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCCCC.C([Li])CCC.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[C:1]1([C:7]#[C:8][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 10821PhenylacetyleneHCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyranHCID 178418339Butyllithium

生成物 1

HCID 148342201-Phenyl-8-(2-tetrahydropyranyloxy)-1-octyne収率 58.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
20 °C

実験手順

To a solution of 11.2 g of phenylacetylene dissolved in 100 ml of tetrahydrofuran, 78.8 ml of 1.6M-hexane solution of n-butyl lithium was added dropwise at 5°-8° C. Then 150 ml of a hexamethylphosphoramide solution containing 29.4 g of 1-bromo-6-(2-tetrahydropyranyloxy)-hexane was added dropwise at 10°-20° C. After stirring at 20° C. for 30 minutes, the reaction mixture was poured into ice-water and extracted with hexane. The organic layer was washed with water, dried and then the organic solvent was distilled off. The residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=10:1), to give 18.3 g of 1-phenyl-8-(2-tetrahydropyranyloxy)-1-octyne as an oily substance.

後処理

  1. additionwas added dropwise at 10°-20° C
  2. extractionextracted with hexane
  3. washThe organic layer was washed with water
  4. customdried
  5. distillationthe organic solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-5198d37285e94e4c917601bdb7bb3bf0
出典データセット
uspto-grants-1989_12
特許番号
US04886817

関連ノート

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