Hydrochloric Acid → 7-(4-hydroxybut-1-ynyl)-9,9-dimethyl-9H-fluoren-2-ol

HRID 511063Notes

Reaction equation

HRID 511063 reaction equation
Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:17])=[CH:10][C:11]=3[C:12]2([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[CH2:18]([OH:22])[CH2:19][C:20]#[CH:21].O.Cl>C1COCC1.C(NC(C)C)(C)C.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>[OH:22][CH2:18][CH2:19][C:20]#[C:21][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:17])=[CH:10][C:11]=3[C:12]2([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 135663-Butyn-1-OLHCID 66798023HCID 66798023, compound

Product 1

HCID 667982407-(4-hydroxybut-1-ynyl)-9,9-dimethyl-9H-fluoren-2-ol

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

14.7 g (0.048 mol) of 7-bromo-9,9-dimethyl-9H-fluoren-2-ol, 1.3 g (1.85 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.5 g (2.6 mmol) of copper(I) iodide are initially introduced in 200 ml of THF and 20 ml of diisopropylamine, and a solution of 9.5 ml (0.13 mmol) of but-3-yn-1-ol in 50 ml of THF is added over the course of 2 h under reflux. When the addition is complete, the batch is heated under reflux for a further 1 h, added to water, acidified using dil. hydrochloric acid and extracted three times with ethyl acetate. The combined org. phases are dried over sodium sulfate, and the solvent is removed in vacuo. Chromatography of the crude product on silica gel with toluene/ethyl acetate (4:1) gives 7-(4-hydroxybut-1-ynyl)-9,9-dimethyl-9H-fluoren-2-ol as colourless oil.

Workup

  1. temperatureunder reflux
  2. additionWhen the addition
  3. temperaturethe batch is heated
  4. temperatureunder reflux for a further 1 h
  5. extractionextracted three times with ethyl acetate
  6. dry with materialphases are dried over sodium sulfate
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c36117577c0344748ce132549f5a10f9
Source dataset
uspto-grants-2015_08
Patent number
US09096795B2

Reaction notes

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