Ammonium Chloride → 1-(6-Fluoropyridin-3-yl)-1-(4-(methylthio)phenyl)ethanol

HRID 1621583Notes

Reaction equation

HRID 1621583 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:18][Mg]Br.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)([OH:9])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66600001(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 666003611-(6-Fluoropyridin-3-yl)-1-(4-(methylthio)phenyl)ethanolYield 102.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanone (1.256 g, 5.079 mmol) was dissolved in THF (19 mL) and the flask was cooled in an ice water bath. Then, methylmagnesium bromide (3.0 M in diethyl ether, 3.40 mL, 10.2 mmol) was added via syringe over 5 min. The reaction was stirred at 0° C. under nitrogen for 20 min, and then was treated with saturated ammonium chloride (2.5 mL, added dropwise at first as gas evolution is observed). The reaction was quenched at 0° C. Then, the reaction was diluted with water (15 mL) and the layers were separated. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum at room temperature overnight to give 1-(6-fluoropyridin-3-yl)-1-(4-(methylthio)phenyl)ethanol (1.375 g). 1H NMR (CDCl3, 400 MHz) δ 8.26 (d, J=2.35 Hz, 1H), 7.82-7.76 (m, 1H), 7.35-7.30 (m, 2H), 7.25-7.20 (m, 2H), 6.86 (dd, J=8.61 Hz, 2.93 Hz, 1H), 2.48 (s, 3H), 2.30 (s, 1H), 1.96 (s, 3H). m/z (ESI, +ve ion) 264 (M+H)+.

Workup

  1. temperaturethe flask was cooled in an ice water bath
  2. additionadded dropwise at first as gas evolution
  3. customThe reaction was quenched at 0° C
  4. additionThen, the reaction was diluted with water (15 mL)
  5. customthe layers were separated
  6. extractionThe aqueous phase was extracted with DCM
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-b650137e6ef94f4a82c5666e34033666
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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