Diisobutylaluminumhydride → HCID 73076084, compound

HRID 235321Notes

Reaction equation

HRID 235321 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([Si:15]([CH3:36])([CH3:35])[O:16][CH:17]1[CH2:22][CH:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:20][C:19]([OH:34])([C:31]([O-])=[O:32])[CH2:18]1)([CH3:14])([CH3:13])[CH3:12]>C1(C)C=CC=CC=1>[C:27]([Si:24]([CH3:26])([CH3:25])[O:23][CH:21]1[CH2:22][CH:17]([O:16][Si:15]([C:11]([CH3:12])([CH3:13])[CH3:14])([CH3:35])[CH3:36])[CH2:18][C:19]([OH:34])([CH2:31][OH:32])[CH2:20]1)([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 23367336HCID 23367336, compound

Product 1

HCID 73076084HCID 73076084, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutyl aluminum hydride (6 mL, 9 mmol, 1.5M in toluene) was added to a solution of the ester 14 (0.56 g, 1.3 mmol) in anhydrous toluene (20 mL) at -78° C. After 20 min the solution was warmed to 0° C. and stirred for 1 h. The solution was slowly quenched by adding to a stirred 0° C. solution of 2N potassium sodium tartrate. Ethyl acetate was added and the organic layer separated and the water phase extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous MgSO4, filtered and evaporated. The material was further purified by column chromatography on silica gel with ethyl acetate hexane mixtures to give the diol 15 (0.3 g, 59%) 1H NMR (CDCl3, 500 MHz) δ0.11 (s, 3H), 0.12 (s, 3H), 0.14 (s, 3H), 0.16 (s, 3H), 0.90 (s, 9H), 0.91 (s, 9H), 1.28 (dd, 1H), 1.43 (dd, 1H), 2.00 (ddd, 3H), 2.16 (dd, 1H), 3.33 (dd, 1H), 3.40 (dd, 1H), 4.34 (m, 2×1H).

Workup

  1. customThe solution was slowly quenched
  2. additionby adding to a stirred 0° C. solution of 2N potassium sodium tartrate
  3. additionEthyl acetate was added
  4. customthe organic layer separated
  5. extractionthe water phase extracted with ethyl acetate
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe material was further purified by column chromatography on silica gel with ethyl acetate hexane mixtures

Sources & evidence

ORD record
ord-7c1aff2fdaaa400393eeaa3ecacc1e9a
Source dataset
uspto-grants-1997_01
Patent number
US05597932

Reaction notes

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