Bromoform → HCID 69642653, compound

HRID 1828087Notes

Reaction equation

HRID 1828087 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][C:10](C=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)Br.[OH-:19].[K+].[O:21]1[CH2:26][CH2:25][O:24][CH2:23]C1.CO>CO>[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([CH:25]([O:24][CH3:23])[C:26]([OH:21])=[O:19])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 114011991-benzyl-1H-pyrazole-3-carbaldehydeHCID 21966525Dioxane Methanol

Product 1

HCID 69642653HCID 69642653, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl-1H-pyrazole-3-carbaldehyde (1.55 g, CAS 321405-31-6) and bromoform (0.94 ml) were dissolved under an argon atmosphere in dioxane/MeOH 1:1 (40 ml) and cooled to 0° C. A solution of KOH (2.31 g) in MeOH (20 ml) were added over a period of 20 min. The reaction was warmed to r.t. and stirred overnight. The reaction mixture was concentrated to one third of the volume, then taken up in water and washed with EtOAc. The aqueous layer was brought ot pH 1 with HCl, then extracted with EtOAc. The organic layer was washed with brine and concentrated to give crude (RS)-(1-benzyl-1H-pyrazol-3-yl)-methoxy-acetic acid (1.41 g). Yellow oil. MS 245.1 ([M−H]−)

Workup

  1. temperatureThe reaction was warmed to r.t.
  2. concentrationThe reaction mixture was concentrated to one third of the volume
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c22297b020848f5b2e490550f5b8d6c
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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