Sodium hydride → HCID 15239101, compound

HRID 274351Notes

Reaction equation

HRID 274351 reaction equation
[H-].[Na+].[CH3:3][CH:4]([O:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1)[CH2:5][CH3:6].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](F)[N:20]=1>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[F:18][C:19]1[N:20]=[C:21]([O:15][CH2:14][CH2:13][O:12][C:11]2[CH:16]=[CH:17][C:8]([O:7][CH:4]([CH3:3])[CH2:5][CH3:6])=[CH:9][CH:10]=2)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 739342,6-DifluoropyridineHCID 13939035HCID 13939035, compound

Product 1

HCID 15239101HCID 15239101, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a mixture of sodium hydride (0.12 g) in 5 ml of THF and 4 ml of HMPA, cooled in an ice bath, is added, dropwise, a solution of 2-[4-(1-methylpropoxy)phenoxy]ethanol (1.00 g) in 5 ml of THF. The mixture is stirred at RT for 2 hours, after which 2,6-difluoropyridine (0.65 g) is added and the mixture is stirred at RT overnight. The THF is removed by rotoevaporation and the product is isolated by column chromatography on silica gel to give 6-fluoro-2-{2-[4-(1-methylpropoxy)phenoxy]ethoxy}pyridine, MS m/e 306 (M+).

Workup

  1. temperaturecooled in an ice bath
  2. additionis added
  3. stirringthe mixture is stirred at RT overnight
  4. customThe THF is removed by rotoevaporation
  5. customthe product is isolated by column chromatography on silica gel

Sources & evidence

ORD record
ord-489ceeb41893462cb82cf90de0ece2b3
Source dataset
uspto-grants-1995_02
Patent number
US05389651

Reaction notes

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