Hydrochloric Acid → HCID 66798230, compound

HRID 1429283Notes

Reaction equation

HRID 1429283 reaction equation
I[C:2]1[CH:15]=[C:14]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:16])=[CH:10][C:11]=3[CH2:12][CH2:13]2)=[CH:4][CH:3]=1.C(NC(C)C)(C)C.C#CCC.Cl.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O>[OH:32][CH2:31][CH2:30][C:29]#[C:33][C:2]1[CH:15]=[C:14]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:16])=[CH:10][C:11]=3[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 78461-ButyneHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 66798094HCID 66798094, compound

Product 1

HCID 66798230HCID 66798230, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

9.0 g (24.6 mmol) of 7-iodo-9,10-dihydrophenanthren-2-ol are initially introduced in 100 ml of THF, 1.0 g (1.43 mmol) of bis(triphenylphosphine)-palladium(II) chloride, 0.3 g (1.58 mmol) of copper(I) iodide and 11 ml of diisopropylamine are added, and a solution of 3.0 g (42.8 mmol) of 1-butyne in 20 ml of THF is subsequently added dropwise with cooling at max. 30° C. The batch is left to stir at room temp. for 1.5 h, added to water and acidified using 2 N hydrochloric acid. The aqueous phase is separated off and extracted three times with ethyl acetate. The combined org. phases are washed with water, dried over sodium sulfate, and the solvent is removed in vacuo. The crude product is filtered through silica gel with dichloromethane/ethyl acetate (3:1) and recrystallised from toluene, giving 7-(4-hydroxybut-1-ynyl)-9,10-dihydrophenanthren-2-ol as a colourless solid.

Workup

  1. temperaturewith cooling at max
  2. custom30° C
  3. waitThe batch is left
  4. customThe aqueous phase is separated off
  5. extractionextracted three times with ethyl acetate
  6. washphases are washed with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent is removed in vacuo
  9. filtrationThe crude product is filtered through silica gel with dichloromethane/ethyl acetate (3:1)
  10. customrecrystallised from toluene

Sources & evidence

ORD record
ord-35b34baf4df5450897b498c9d526986c
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

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