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

HRID 477007

반응식

HRID 477007 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5198d37285e94e4c917601bdb7bb3bf0
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886817

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