Lithium tri-tert-butoxyaluminohydride → HCID 19746854, compound

HRID 2253930Notes

Reaction equation

HRID 2253930 reaction equation
[CH2:1]([C:4]([OH:24])([CH2:21][CH:22]=[CH2:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18])[CH:2]=[CH2:3].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>O1CCCC1>[CH2:1]([C:4]([OH:24])([CH2:21][CH:22]=[CH2:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:19])([CH3:20])[CH2:17][OH:18])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 19746849HCID 19746849, compound

Product 1

HCID 19746854HCID 19746854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.01 g (3.0 mmol) of the title compound of Example 7 and 2.5 g (10 mmol) of lithium tris-t-butoxyaluminum hydride in 250 mL of tetrahydrofuran under N2 was stirred overnight at room temperature. After dilution with ether the mixture was washed sequentially with saturated solutions of Na-K tartrate, NaCl, then dried and the solvents removed. The residue was dissolved in 100 mL of Skellysolve A, decolorized with activated charcoal, the mixture filtered and the filtrate evaporated. The residue was dried at 40°/3 mm to yield 0.92 g of a cloudy oil.

Workup

  1. washAfter dilution with ether the mixture was washed sequentially with saturated solutions of Na-K tartrate, NaCl
  2. customdried
  3. customthe solvents removed
  4. dissolutionThe residue was dissolved in 100 mL of Skellysolve A
  5. filtrationthe mixture filtered
  6. customthe filtrate evaporated
  7. customThe residue was dried at 40°/3 mm
  8. customto yield 0.92 g of a cloudy oil

Sources & evidence

ORD record
ord-9cd9814ba1304f5c873a9e934160391d
Source dataset
uspto-grants-1993_08
Patent number
US05233063

Reaction notes

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