Water → HCID 59456303, compound

HRID 1873426Notes

Reaction equation

HRID 1873426 reaction equation
C([Si](C(C)C)(C(C)C)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[Se:16][C:15]([CH2:17][OH:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[OH:18][CH2:17][C:15]1[Se:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86644792HCID 86644792, compound

Product 1

HCID 59456303HCID 59456303, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.7 g (21.4 mmol) of [5-(4-triisopropylsilanyloxyphenyl)selenophen-2-yl]-methanol are initially introduced in 200 ml of THF, and 50 ml of TBAF (50 mmol, 1 M soln. in THF) are added with ice-cooling. After 30 min at this temperature, the mixture is added to water and extracted with MTBE. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is recrystallised from ethyl acetate. 4-(5-Hydroxymethylselenophen-2-yl)phenol is obtained as a beige solid.

Workup

  1. temperaturecooling
  2. extractionextracted with MTBE
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted with MTBE
  5. washThe combined organic phases are washed with sat. sodium chloride soln
  6. customand dried
  7. concentrationThe solution is concentrated to dryness
  8. customthe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-c7d5dc7d917d420ca1d23f2ed75fa568
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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