Diisobutylaluminum hydride → HCID 86635037, compound

HRID 2088399Notes

Reaction equation

HRID 2088399 reaction equation
CC(C[AlH]CC(C)C)C.C([O:12][C:13]([C@@H:15]1[CH2:19][C:18]([C:20]2[CH:25]=[CH:24][C:23](C)=[CH:22][N:21]=2)=[C:17]([CH3:27])[C@H:16]1[O:28][Si:29]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31])=O)C>C1(C)C=CC=CC=1>[CH3:27][C:17]1[C@@H:16]([O:28][Si:29]([CH2:30][CH3:31])([CH2:34][CH3:35])[CH2:32][CH3:33])[C@H:15]([CH:13]=[O:12])[CH2:19][C:18]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67267363HCID 67267363, compound

Product 1

HCID 86635037HCID 86635037, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of DIBAL-H (0.44 ml, 1.0 M in hexane, 0.44 mmol, 1.1 equiv) was added dropwise to a solution of silyl ether 29b (150 mg, 0.4 mmol) in toluene (2 ml) at −78° C. The reaction mixture was stirred at that temperature for 1 hr and quenched by dropwise addition of saturated NH4Cl solution (0.2 ml). The reaction mixture was allowed to reach room temperature and a saturated solution of Rochelle salt (1 ml) and brine (0.4 ml) were added. The mixture was extracted with ethyl acetate (3×2 ml) and the combined organic extracts were dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to give crude aldehyde 30b as a yellow liquid which was used in the next step without further purification.

Workup

  1. customquenched by dropwise addition of saturated NH4Cl solution (0.2 ml)
  2. customto reach room temperature
  3. additiona saturated solution of Rochelle salt (1 ml) and brine (0.4 ml) were added
  4. extractionThe mixture was extracted with ethyl acetate (3×2 ml)
  5. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f5add728f7f548e7b380ad116cc023eb
Source dataset
uspto-grants-2013_05
Patent number
US08435983B2

Reaction notes

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