267875-65-0|2,2-Difluoro-2-(pyridin-2-yl)ethanol| Ambeed

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CAS No. :	267875-65-0
Formula :	C₇H₇F₂NO
M.W :	159.13
SMILES Code :	FC(C1=NC=CC=C1)(F)CO
MDL No. :	MFCD09038169
InChI Key :	RTZZBUQTHNQTSR-UHFFFAOYSA-N
Pubchem ID :	9942216

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; pentane;	Step H 2,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate (1-8) To a stirred -78° C. solution of 50 mg (0.31 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol and 100 mg (0.49 mmol) of 2,6-di-t-butyl-4-methylpyridine in 1.0 ml of CH2Cl2 was added dropwise 79 muL (0.47 mmol) of trifluoromethansulfonic anhydride. After the addition, the cold bath was removed, and stirring continued for 0.5 h. The reaction was diluted with 2 ml of pentane, and the resulting precipitate washed with pentane. The filtrate was evaporated in vacuo to dryness to give as a yellow solid: 1H NMR (CDCl3) delta8.66 (d, 1H, 4.9 Hz), 7.89 (td,1H, 7.7, 1.7 Hz), 7.76 (d, 1H, 7.9 Hz), 7.45-7.49 (m, 1H), 5.12 (t, 2 H, 11.9 Hz).
	In dichloromethane; pentane;	Step B 2,2-Difluoro-2-(2-pyridyl)ethyl Trifluoromethanesulfonate To a stirred -78° solution of 50 mg (0.31 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol and 100 mg (0.49 mmol) of 2,6-di-t-butyl-4-methylpyridine in 1.0 mL of CH2Cl2 was added 79 muL (0.47 mmol) of trifluoromethansulfonic anhydride dropwise under Ar. After the addition, the cold bath was removed, and stirring continued for 0.5 h. The reaction was diluted with 2 mL of pentane, and the resulting precipitate washed with pentane. The filtrate was evaporated in vacuo to dryness to give the title compound as a yellow solid: 1H NMR (CDCl3) delta 8.66 (d, 1H, 4.9 Hz), 7.89 (td, 1H, 7.7, 1.7 Hz), 7.76 (d, 1H, 7.9 Hz), 7.45-7.49 (m, 1H), 5.12 (t, 2; H, 11.9 Hz).

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane; pentane;	2,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate (I-1-4) To a stirred solution of 5 g (31.4 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol I-1-3 and 9.69 g (47.2 mmol) of 2,6-di-t-butyl-4-methylpyridine in 110 mL of methylene chloride at -78° C. under Ar was added 7.93 mL (47.2 mmol) of triflic anhydride dropwise. After 1 h, the reaction was diluted with 100 mL of pentane and filtered. The filtrate was concentrated and treated again with pentane and filtered. Concentration of the filtrate gave I-1-4 as a brown oil, contaminated with 2,6-di-t-butyl-4-methylpyridine: 1H NMR (CDCl3) delta5.12 (t, 2H), 7.45-7.5 (m, 1H), 7.75 (d,1H), 7.86-7.94 (m, 1H), 8.65 (d, 1H).
	With trifluoromethylsulfonic anhydride; In dichloromethane; pentane;	Step E 2,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate (5a) To a stirred solution of 5 g (31.4 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol 5 and 9.69 g (47.2 mmol) of 2,6-di-t-butyl-4-methylpyridine in 110 mL of methylene chloride at -78° C. under Ar was added 7.93 mL (47.2 mmol) of triflic anhydride dropwise. After 1 h, the reaction was diluted with 100 mL of pentane and filtered. The filtrate was concentrated and treated again with pentane and filtered. Concentration of the filtrate gave 5a as a brown oil, contaminated with 2,6-di-t-butyl-4-methylpyridine: 1H NMR (CDCl3) delta5.12 (t, 2H), 7.45-7.5 (m, 1H), 7.75 (d, 1H), 7.86-7.94 (m, 1H), 8.65 (d, 1H).
	With trifluoromethylsulfonic anhydride; In dichloromethane; pentane;	2,2-Difluoro-2-(2-pyridyl)ethyl Trifluoromethanesulfonate (1-4). To a stirred solution of 5 g (31.4 mmol) of 2,2-difluoro-2-(2-pyridyl)ethanol 1-3 and 9.69 g (47.2 mmol) of 2,6-di-t-butyl-4-methylpyridine in 110 mL of methylene chloride at -78° C. under Ar was added 7.93 mL (47.2 mmol) of triflic anhydride dropwise. After 1 h, the reaction was diluted with 100 mL of pentane and filtered. The filtrate was concentrated and treated again with pentane and filtered. Concentration of the filtrate gave 1-4 as a brown oil, contaminated with 2,6-di-t-butyl-4-methylpyridine: 1H NMR (CDCl3) delta 5.12 (t, 2H), 7.45-7.5 (m, 1H), 7.75 (d, 1H), 7.86-7.94 (m, 1H), 8.65 (d, 1H).

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CAS No.: 267875-65-0

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CAS No.: 267875-65-0

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