Sodium Hydroxide → HCID 57659574, compound

HRID 1172587Notes

Reaction equation

HRID 1172587 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH2:10][C:11]1[N:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:13]=[C:14]([CH3:16])[CH:15]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH2:17]([N:12]1[C:11]([CH2:10][CH2:9][OH:8])=[CH:15][C:14]([CH3:16])=[N:13]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57659581HCID 57659581, compound

Product 1

HCID 57659574HCID 57659574, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

LAH (250 mg, 6.6 mmol) was suspended in THF (18 ml) in an inert atmosphere and cooled to 0° C. followed by the dropwise addition of a solution of (2-benzyl-5-methyl-2H-pyrazol-3-yl)-acetic acid methyl ester (1.07 g, 4.4 mmol) in THF (4 ml). Stirring was continued for 2 h at rt. At 0° C., water (0.25 ml), 15% aqueous NaOH-solution (0.25 ml) and again water (0.75 ml) were subsequently added. Stirring was continued for several hours followed by the addition of sodium sulfate and filtration. The filtrate was concentrated under reduced pressure to give 850 mg (89%) of 2-(2-benzyl-5-methyl-2H-pyrazol-3-yl)-ethanol directly used in the next step without further purification. LC-MS: tR=0.66 min; [M+H]+=217.15.

Workup

  1. stirringStirring
  2. waitwas continued for several hours
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e7f73e161e945c1b2c370aa7f13626f
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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