Tetrabutylammonium Fluoride → HCID 67123218, compound

HRID 2168854Notes

Reaction equation

HRID 2168854 reaction equation
C([Si](C(C)C)(C(C)C)[O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]#[C:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=1)[CH:10]=[CH:9]2)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:27][CH2:26][CH2:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]#[C:16][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[CH:7]=[C:6]([OH:5])[CH:15]=[CH:14]3)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67123251HCID 67123251, compound

Product 1

HCID 67123218HCID 67123218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.0 g (17.4 mmol) of 3-[4-(6-triisopropylsilanyloxynaphthalen-2-ylethynyl)-phenyl]propan-1-ol are dissolved in 100 ml of THF, and 22 ml (22 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF are added with ice-cooling. After 30 min, the cooling is removed, and the batch is left to stir for 1 h at room temp. The batch is added to water, acidified using dil. hydrochloric acid and extracted three times with ethyl acetate. The combined org. phases are dried over sodium sulfate, the solvent is removed in vacuo, and the residue is chromatographed on silica gel with toluene/ethyl acetate/ethanol (60:39:1). Crystallisation of the crude product from toluene gives 6-[4-(3-hydroxypropyl)phenylethynyl]naphthalen-2-ol as a colourless solid.

Workup

  1. temperaturecooling
  2. customthe cooling is removed
  3. waitthe batch is left
  4. additionThe batch is added to water
  5. extractionextracted three times with ethyl acetate
  6. dry with materialphases are dried over sodium sulfate
  7. customthe solvent is removed in vacuo
  8. customthe residue is chromatographed on silica gel with toluene/ethyl acetate/ethanol (60:39:1)
  9. customCrystallisation of the crude product from toluene

Sources & evidence

ORD record
ord-cd7caa2177c745939a88d756c1babdf9
Source dataset
uspto-grants-2015_06
Patent number
US09045683B2

Reaction notes

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