Diisobutylaluminum hydride → 3-[4-(Hydroxymethyl)phenyl]-5-(4-phenyl-5-trifluoromethyl-2-thienyl)-1,2,4-oxadiazole

HRID 1454330Notes

Reaction equation

HRID 1454330 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[S:17][C:18]([C:27]([F:30])([F:29])[F:28])=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)(OC)=[O:2].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:2][CH2:1][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[S:17][C:18]([C:27]([F:30])([F:29])[F:28])=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 113278703-[4-(Carbomethoxy)phenyl]-5-(4-phenyl-5-trifluoromethyl-2-thienyl)-1,2,4-oxadiazole

Product 1

HCID 111538793-[4-(Hydroxymethyl)phenyl]-5-(4-phenyl-5-trifluoromethyl-2-thienyl)-1,2,4-oxadiazoleYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 390 mg (0.91 mmol) of 3-[4-(carbomethoxy)phenyl]-5-(4-phenyl-5-trifluoromethyl-2-thienyl)-1,2,4-oxadiazole (from Step D) in 10 mL of CH2Cl2 at −78° C. was treated with 2.7 mL of 1.0 M DIBALH solution in CH2Cl2. The resulting solution was stirred cold for 1 h, then quenched with 5 mL of sat'd Rochelle salt solution. The mixture was partitioned between 100 mL CH2Cl2 and 50 mL of 1 N NaOH. The organic layer was separated, dried and concentrated. Chromatography on a Biotage 40 S cartridge using 4:1 v/v hexanes/EtOAc (1L) as the eluant afforded 325 mg (89%) of the title compound: 1H NMR (500 Mhz) δ 1.80 (app s, 1H), 4.80 (d, J=4.0, 2H), 7.46-7.48 (5H), 7.52 (d, J=8.0, 2H), 7.91 (q, J=1.5, 1H), 8.14 (d, J=8.0, 2H).

Workup

  1. customquenched with 5 mL of sat'd Rochelle salt solution
  2. customThe mixture was partitioned between 100 mL CH2Cl2 and 50 mL of 1 N NaOH
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bca4e6f5b8c2497c944d3bcd07b360ee
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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