Diisobutylaluminumhydride → 2-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenyl)ethanol

HRID 909917Notes

Reaction equation

HRID 909917 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](OC)=[O:20])=[CH:14][C:13]=1[C:23]1[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=1>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][C:13]=1[C:23]1[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59290381Methyl 2-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenyl)acetate

Product 1

HCID 592904762-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of diisobutylaluminium hydride in dichloromethane (1M, 35 mL) was added dropwise to a stirred solution of methyl 2-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenyl)acetate [Example 13, Step ii)] (3.36 g) in dichloromethane (15 mL) keeping temp of reaction mixture at gentle reflux. The mixture was stirred for 15 min. and carefully quenched by dropwise addition of MeOH (3 mL). The mixture was poured onto 2M HCl (100 mL) and extracted with a mixture DCM/MeOH (9:1, 5×50 mL). The organic was dried over magnesium sulfate, filtered and evaporated to afford 2-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenyl)ethanol (2.2 g) that was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.78 (s, 1H), 7.39 (d, J=7.3 Hz, 1H), 7.09-7.02 (m, 2H), 3.97 (s, 3H), 3.88 (t, J=6.5 Hz, 2H), 2.87 (t, J=6.4 Hz, 2H)

Workup

  1. customtemp of reaction mixture at gentle reflux
  2. customcarefully quenched by dropwise addition of MeOH (3 mL)
  3. additionThe mixture was poured onto 2M HCl (100 mL)
  4. extractionextracted with a mixture DCM/MeOH (9:1, 5×50 mL)
  5. dry with materialThe organic was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4d1d86e6061b460bb30612e0fecb9d4d
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

Loading…