Diisobutylaluminumhydride → HCID 68834825, compound

HRID 1987538Notes

Reaction equation

HRID 1987538 reaction equation
C[O:2][C:3]([C:5]1[C@H:9]([CH2:10][Si:11]([CH3:19])([CH3:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:8]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:7][CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>>[CH3:27][C:24]([Si:21]([CH3:23])([CH3:22])[O:20][C@@H:8]1[C@@H:9]([CH2:10][Si:11]([CH3:19])([CH3:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:5]([CH2:3][OH:2])=[CH:6][CH2:7]1)([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68839731HCID 68839731, compound

Product 1

HCID 68834825HCID 68834825, compoundYield 100%

Procedure

To a solution of 43 (15 g, 37.13 mmol) in hexanes (100 mL) was added diisobutylaluminum hydride (113 mL, 113.4 mmol, 1 N in hexanes) at −78° C. slowly over a period of 30 minutes keeping the temperature below −60° C. The resulting mixture was stirred for 2 hours at the same temperature to complete the reaction. The reaction mixture was quenched by addition of sodium hydroxide (2 N, 200 mL). The organic layer was separated and washed with water, brine, and dried over magnesium sulfate. The organic layer was concentrated in vacuo to dryness to give the crude title compound (13 g, 100% yield).

Workup

  1. customthe temperature below −60° C
  2. customthe reaction
  3. customThe reaction mixture was quenched by addition of sodium hydroxide (2 N, 200 mL)
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe organic layer was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-ab143a3e9b69483d90de5eeec7df76e2
Source dataset
uspto-grants-2009_06
Patent number
US07550619B2

Reaction notes

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