Diisobutylaluminum hydride → HCID 19002879, compound

HRID 2259497Notes

Reaction equation

HRID 2259497 reaction equation
[Br:1][C:2]1[C:6]2=[N:7][C:8]([C:11](OC)=[O:12])=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[C:6]2=[N:7][C:8]([CH2:11][OH:12])=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 15290716HCID 15290716, compound

Product 1

HCID 19002879HCID 19002879, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a -78° C. solution of the methyl ester (0.388 g, 1.42 mmol) of Step 1 in 5 mL of THF was added DIBAL (3.55 mmol) over 5 min. The reaction mixture was left 30 min after which time the solution was brought to 0° C. and quenched with MeOH. Sodium potassium tartrate solution was added and the mixture extracted with EtOAc. The organic phase was dried over Na2SO4, and the solvent evaporated. The crude oil was purified by flash chromatography on silica with EtOAc:hexane 2:3 to give 0.338 g (98%) of the title alcohol.

Workup

  1. customwas brought to 0° C.
  2. customquenched with MeOH
  3. additionSodium potassium tartrate solution was added
  4. extractionthe mixture extracted with EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customthe solvent evaporated
  7. customThe crude oil was purified by flash chromatography on silica with EtOAc:hexane 2:3

Sources & evidence

ORD record
ord-1ae8e2a1556746158704c0a2c7e67a47
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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