Water → HCID 68841498, compound

HRID 1948624Notes

Reaction equation

HRID 1948624 reaction equation
C([Si](CC)(CC)[C:4]1[NH:12][C:7]2=[CH:8][N:9]=[CH:10][CH:11]=[C:6]2[C:5]=1[CH2:13][CH2:14][OH:15])C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1.O>[NH:12]1[C:7]2=[CH:8][N:9]=[CH:10][CH:11]=[C:6]2[C:5]([CH2:13][CH2:14][OH:15])=[CH:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium Fluoride2×HCID 15350907HCID 15350907, compound

Product 1

HCID 68841498HCID 68841498, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-(triethylsilyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)ethanol (1.99 g, 7.24 mmole) was dissolved in THF (17 ml) and TBAF (7.96 ml, 7.96 mmole; 1 M solution in THF) was added at 0° C. The mixture was stirred for 1 hour at 0° C. and then heated to RT. Further TBAF (7.96 ml, 7.96 mmole, 1 M solution in THF) and H2O (5 drops) were added. After 2 days at RT 20 ml of H2O were added and the aqueous phase was extracted with DCM (3×60 ml). The organic phases were combined and washed with saturated NaCl solution (2×20 ml) and dried over MgSO4. After filtering off the drying agent the solvents were removed on a rotary evaporator and the residue was purified by column chromatography (DCM/MeOH=4:1). 2-(1H-pyrrolo[2,3-c]pyridin-3-yl)ethanol (0.60 g, 51%) was formed as a colourless oil, which solidified over time.

Workup

  1. temperatureheated to RT
  2. extractionthe aqueous phase was extracted with DCM (3×60 ml)
  3. washwashed with saturated NaCl solution (2×20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtering off the drying agent the solvents
  6. customwere removed on a rotary evaporator
  7. customthe residue was purified by column chromatography (DCM/MeOH=4:1)

Sources & evidence

ORD record
ord-ee264ca9ea144093a3aa55015786f5c3
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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