Diisobutylaluminum hydride → HCID 21865558, compound

HRID 857275Notes

Reaction equation

HRID 857275 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([Br:16])[CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)=O)C.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O>C(Cl)Cl>[Br:16][C:14]1[CH:15]=[C:6]([CH:4]=[O:3])[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 38061142,3-DihydroxybutanedioateHCID 58759778HCID 58759778, compound

Product 1

HCID 21865558HCID 21865558, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 8-bromo-quinoline-6-carboxylic acid ethyl ester (1.0 eq) in CH2Cl2 (0.26M) at −78° C. was added dropwise DIBAL (neat; 2.0 eq). The resulting mixture was stirred 1 h at −78° C. then poured in Na/K tartrate (2N) and stirred for 2 h. The mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to afford the desired compound along with the corresponding hydroxymethyl analog. To the mixture dissolved in EtOAc (0.45M) was added MnO2 (2.5 eq). The resulting mixture was refluxed for 1 h, cooled to room temperature, filtered on a pad of silica gel and concentrated. The residual solid was vigorously stirred in Hex/Et2O (2/1) for 2 h to afford following filtration the desired compound as a light yellow solid.

Workup

  1. stirringstirred for 2 h
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ec8b48c92244287aeb5a022667415aa
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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