Hydrochloric Acid → HCID 66798230, compound

HRID 511060Notes

Reaction equation

HRID 511060 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.[CH2:24]([OH:28])[CH2:25][C:26]#[CH:27].Cl>C1COCC1.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:28][CH2:24][CH2:25][C:26]#[C:27][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 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 135663-Butyn-1-OLHCID 66798094HCID 66798094, compound

Product 1

HCID 66798230HCID 66798230, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

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 subsequently a solution of 3.0 g (42.8 mmol) of but-3-yn-1-ol in 20 ml of THF is added dropwise at max. 30° C. with gentle cooling. 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 colourless solid.

Workup

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

Sources & evidence

ORD record
ord-57be430b8a664c8d92af4503c09059a0
Source dataset
uspto-grants-2015_08
Patent number
US09096795B2

Reaction notes

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