Diisobutylaluminumhydride → HCID 22803365, compound

HRID 372116Notes

Reaction equation

HRID 372116 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[CH2:43][O:42][C:13]([CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([CH2:14][CH2:15][C@H:16]2[C@H:23]([O:24]C(=O)C3C=CC=CC=3)[CH2:22][C@H:21]3[C@@H:17]2[CH2:18][C:19](=[O:33])[O:20]3)[O:12]1>C1(C)C=CC=CC=1>[CH2:43]1[CH2:11][O:12][C:13]([CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([CH2:14][CH2:15][C@@H:16]2[C@@H:17]3[C@@H:21]([O:20][CH:19]([OH:33])[CH2:18]3)[CH2:22][C@H:23]2[OH:24])[O:42]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 22803339HCID 22803339, compound

Product 1

HCID 22803365HCID 22803365, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

At -60° under argon, 16 ml. of a 20% solution of diisobutylaluminum hydride in toluene was added dropwise to a solution of 1.65 g. of (1S,5R,6R,7R)-6-(3,3-ethylenedioxy-4-phenoxy-1-butyl)-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one (produced in accordance with Example 2[a]) in 100 ml. of absolute toluene; the mixture was stirred for 30 minutes. By the dropwise addition of 5 ml. of isopropanol, the reaction was terminated, and the mixture was stirred for 30 minutes at 0° while adding 100 ml. of brine. Then, the mixture was extracted with ethyl acetate, shaken with brine, dried with magnesium sulfate, and evaporated under vacuum. Filtration of the residue with ether over 35 g. of silica gel yielded 1.1 g. of the title compound as a colorless oil. IR: 3600,1500 cm-1.

Workup

  1. customAt -60°
  2. additionBy the dropwise addition of 5 ml
  3. customof isopropanol, the reaction was terminated
  4. stirringthe mixture was stirred for 30 minutes at 0°
  5. additionwhile adding 100 ml
  6. extractionThen, the mixture was extracted with ethyl acetate
  7. stirringshaken with brine
  8. dry with materialdried with magnesium sulfate
  9. customevaporated under vacuum
  10. filtrationFiltration of the residue with ether over 35 g
  11. customof silica gel yielded 1.1 g

Sources & evidence

ORD record
ord-8b7c1df132b54a8da8bf2518f8b44e65
Source dataset
uspto-grants-1978_05
Patent number
US04088775

Reaction notes

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