Diisobutylaluminumhydride → HCID 54176324, compound

HRID 1612947Notes

Reaction equation

HRID 1612947 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14](=O)[CH:15]=[CH:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21]([Br:23])[CH:22]=1)C>CCOCC>[Br:23][C:21]1[CH:22]=[C:17]([CH:16]=[CH:15][CH2:14][OH:13])[CH:18]=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 53942077HCID 53942077, compound

Product 1

HCID 54176324HCID 54176324, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diisobutylaluminum hydride (DIBAL-H, 8.02 mls, 1.54M in toluene) in ether (50 mls) is cooled to -78° C. under N2. A solution of 3-(5-bromo-3-pyridinyl)-2-propenoic acid ethyl ester [see Nishikawa, Y., et al.(1989) J. Med. Chem. 32, 583-593] (1.54 gms, 6.00 mmol) in ether (50 mls) is added. After one hour the dry ice/acetone bath is removed and the mixture is diluted with methylene chloride, dried over Na2SO4, evaporated and chromatographed (1:1 ethyl acetate:hexane followed by 2:1 ethyl acetate:hexane) to yield 1.08 gms of an oil (84%). 1H NMR (DMSO, 300 MHz) δ8.60 (s, 1H), 8.50 (s, 1H), 8.15 (s, 1H), 6.60 (m, 2H), 5.00 (s, 1), and 4.10 (d, J=3.8 Hz, 2H).

Workup

  1. customAfter one hour the dry ice/acetone bath is removed
  2. additionthe mixture is diluted with methylene chloride
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customchromatographed (1:1 ethyl acetate:hexane followed by 2:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-32a7322300be43b786a4f5375f003af6
Source dataset
uspto-grants-1993_03
Patent number
US05191084

Reaction notes

Loading…