HCID 15453926, compound → HCID 15453927, compound

HRID 1740515Notes

Reaction equation

HRID 1740515 reaction equation
[CH2:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[O:17][CH2:18][O:19][CH3:20])=[C:8]([C:21](OC)=[O:22])[CH:7]=[N:6]1)[CH2:2][CH2:3][CH3:4].CC(C[Al]CC(C)C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[O:17][CH2:18][O:19][CH3:20])=[C:8]([CH2:21][OH:22])[CH:7]=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 15453926HCID 15453926, compoundHCID 16682954Dibah

Product 1

HCID 15453927HCID 15453927, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Methyl 1-n-butyl-5-(4-chloro-2-methoxymethoxyphenyl)-1H-pyrazol-4-yl carboxylate (10.00 g, 0.028 mol) in 200 mL of CH2Cl2 at 0° C. was added 85.2 mL of 1.5 M Dibal-H in toluene. After stirring for 1 h, the reaction was quenched with MeOH (100 mL) followed by addition of 35 mL of conc. HCl in 200 mL of water. The resulting mixture was stirred for 15 min. and extracted with CH2Cl2 (3×200 mL). The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave 9.50 g (97%) of the title compound as a oil: MS (ESI) m/z 325 (M+H)+ ; 1H NMR (400 MHz, CDCl3) d 7.63 (s, 1H), 7.13-7.29 (m,3H), 5.09 (s, 2H), 4.36 (dd, 2H), 3.80-3.98 (m, 2H), 3.35 (s, 3H), 1.70 (m, 2H), 1.18 (m, 2H), 0.81 (t, 3H).

Workup

  1. customthe reaction was quenched with MeOH (100 mL)
  2. additionfollowed by addition of 35 mL of conc. HCl in 200 mL of water
  3. stirringThe resulting mixture was stirred for 15 min.
  4. extractionextracted with CH2Cl2 (3×200 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-abaeb3445b9d4397a013e8a9f244ca55
Source dataset
uspto-grants-1999_10
Patent number
US05969151

Reaction notes

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