Triethylamine → HCID 57420504, compound

HRID 1271206Notes

Reaction equation

HRID 1271206 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27583132-(3,4-Difluorophenyl)ethan-1-ol

Product 1

HCID 57420504HCID 57420504, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3,4-difluoro-phenyl)-ethanol (1.00 g, 6.33 mmol) in tetrahydrofuran (63.0 mL) at 0° C. was added triethylamine (1.95 mL, 13.9 mmol) followed by methanesulfonyl chloride (0.538 mL, 6.96 mmol). The solution was allowed to warm to room temperature overnight, quenched with water (20 mL), and diluted with ethyl acetate (100 mL). The layers were separated and the aqueous phase was extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with saturated NaHCO3 (1×20 mL), brine (1×20 mL), dried over MgSO4, filtered, and concentrated to give the title compound. 1H NMR (CDCl3) δ 2.92 (s, 3H), 3.01 (t, J=6.59 Hz, 2H), 4.37–4.40 (m, 2H), 6.94–6.97 (m, 1H), 7.03–7.06 (m, 1H), 7.07–7.15 (m, 1H) ppm. 19F NMR (CDCl3) 8–140.48–, 137.71 ppm.

Workup

  1. customquenched with water (20 mL)
  2. additiondiluted with ethyl acetate (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×25 mL)
  5. washThe combined organic extracts were washed with saturated NaHCO3 (1×20 mL), brine (1×20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-21c2dfce84f6401e9637c1f48ed7a312
Source dataset
uspto-grants-2007_04
Patent number
US07205295B2

Reaction notes

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