Hexane → HCID 58081245, compound

HRID 928374Notes

Reaction equation

HRID 928374 reaction equation
[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][C:8]=2[O:17][CH3:18])[CH:5]=[CH:4][CH:3]=[N:2]1.CCCCCC>C1COCC1>[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:10]([CH2:11][OH:12])=[CH:9][C:8]=2[O:17][CH3:18])[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 8058HexaneHCID 58081197HCID 58081197, compound

Product 1

HCID 58081245HCID 58081245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of methyl 4-((1H-pyrazol-1-yl)methyl)-3-methoxybenzoate (330 mg crude) in THF (6 ml) DIBAL-H 1M in Hexane (4.02 ml, 4.02 mmol) was added dropwise at −70° C. The reaction mixture was stirred at −70° C. for 3.5 h. The reaction mixture was quenched subsequently with ethyl acetate (2 ml) and saturated aqueous NH4Cl. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude (4-((1H-pyrazol-1-yl)methyl)-3-methoxyphenyl)methanol. MS [M+H]+=219.

Workup

  1. customThe reaction mixture was quenched subsequently with ethyl acetate (2 ml) and saturated aqueous NH4Cl
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab0accfa85ae402aa83a58d1bbda327a
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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