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

HRID 477007

Reaction equation

HRID 477007 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5198d37285e94e4c917601bdb7bb3bf0
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Linked notes

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