Diisobutylaluminum hydride → HCID 11081513, compound

HRID 2428054Notes

Reaction equation

HRID 2428054 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][O:11][C@@H:12]1[O:17][C@@H:16]([CH2:18][CH2:19]/[CH:20]=[CH:21]\[C@@H:22]([C@@H:24]2[C@@H:29]([CH3:30])[CH2:28][O:27][CH:26]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[O:25]2)[CH3:23])[C@H:15]([CH3:39])[C@H:14]([O:40][CH2:41][O:42][CH3:43])[C@H:13]1[CH3:44].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:26][O:25][C@@H:24]([C@@H:22]([CH3:23])/[CH:21]=[CH:20]\[CH2:19][CH2:18][C@H:16]2[C@H:15]([CH3:39])[C@H:14]([O:40][CH2:41][O:42][CH3:43])[C@@H:13]([CH3:44])[C@H:12]([O:11][CH3:10])[O:17]2)[C@@H:29]([CH3:30])[CH:28]=[O:27])=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 159087TriacetoxyperiodinaneHCID 67148173HCID 67148173, compound

Product 1

HCID 11081513HCID 11081513, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DIBAL (1.0 M in hexane, 2.1 mL, 2.1 mmol) was added dropwise to a solution of the acetal 36 (329 mg, 0.67 mmol) in dry CH2Cl2 (6.7 mL) at 0° C. After the mixture was stirred for 2 h, the reaction was quenched with saturated aqueous sodium tartrate (20 mL) followed by vigorous stirring for several hours. The aqueous phase was extracted with CH2Cl2 (3×10 mL) and the combined organic layers were washed with brine (10 mL). After drying over MgSO4 and evaporation under vacuum, the residue was used for the next reaction without further purification. The crude alcohol in CH2Cl2 (13 mL) was treated with Dess-Martin periodinane (340.8 mg, 0.80 mmol). After the reaction was complete, the mixture was quenched with saturated NaHCO3 (20 mL). The aqueous layer was extracted with CH2Cl2 (2×10 mL) and the combined extracts were dried over anhydrous MgSO4. Filtration and concentration followed by short flash column chromatography filtration (hexane/EtOAc 9:1) provided crude aldehyde 38 (267 mg, 81%) as a colorless oil which was used without further purification.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium tartrate (20 mL)
  2. stirringby vigorous stirring for several hours
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  4. washthe combined organic layers were washed with brine (10 mL)
  5. dry with materialAfter drying over MgSO4 and evaporation under vacuum
  6. customthe residue was used for the next reaction without further purification
  7. customthe mixture was quenched with saturated NaHCO3 (20 mL)
  8. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  9. dry with materialthe combined extracts were dried over anhydrous MgSO4
  10. filtrationFiltration and concentration
  11. filtrationfollowed by short flash column chromatography filtration (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-e829f1afade84f8ab174123bf155bff0
Source dataset
uspto-grants-2011_06
Patent number
US07968736B2

Reaction notes

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