Sodium Hydroxide → HCID 67436691, compound

HRID 1890260Notes

Reaction equation

HRID 1890260 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][CH2:8][CH2:9][N:10]1[C:14]([C:15](OC)=[O:16])=[CH:13][C:12]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[N:11]1.[OH-].[Na+].[H][H]>O1CCCC1>[Cl:7][CH2:8][CH2:9][N:10]1[C:14]([CH2:15][OH:16])=[CH:13][C:12]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[N:11]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67438061HCID 67438061, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67436691HCID 67436691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon and at 0° C., 4 ml of lithium aluminium hydride solution (1M in diethyl ether, 4.00 mmol) are added to a solution of 1.1 g (4.00 mmol) of methyl 1-(2-chloroethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxylate in 20 ml of tetrahydrofuran. The mixture is then stirred at 0° C. for 2 h. At 0° C., 5M of aqueous NaOH solution are then carefully added dropwise to the reaction mixture until the evolution of hydrogen has stopped. The suspension formed is decanted off and the solvent is removed. The crude product obtained is purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 900 mg (86%) of the desired product; log P(HCOOH): 1.84; 1H-NMR (MeCN-d3): δ=7.81-7.77 (m, 2H), 7.16-7.12 (m, 2H), 6.53 (s, 1H), 4.64 (d, 2H), 4.45 (t, 2H), 4.00 (t, 2H).

Workup

  1. customThe suspension formed
  2. customis decanted off
  3. customthe solvent is removed

Sources & evidence

ORD record
ord-b6fff0136f8b4b009e52cb72fdd339f7
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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