Toluene → HCID 22803368, compound

HRID 372119Notes

Reaction equation

HRID 372119 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[CH2:45][O:44][C:13]([CH2:32][O:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=2)(/[CH:14]=[CH:15]/[C@H:16]2[C@H:23]([O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[CH2:22][C@H:21]3[C@@H:17]2[CH2:18][C:19](=[O:31])[O:20]3)[O:12]1.C1(C)C=CC=CC=1.C(O)(C)C>O>[CH2:45]1[CH2:11][O:12][C:13]([CH2:32][O:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=2)(/[CH:14]=[CH:15]/[C@@H:16]2[C@@H:17]3[C@@H:21]([O:20][CH:19]([OH:31])[CH2:18]3)[CH2:22][C@H:23]2[O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[O:44]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3776IsopropanolHCID 21225700DiisobutylaluminumhydrideHCID 22803348HCID 22803348, compound

Product 1

HCID 22803368HCID 22803368, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon at -70°, 1.5 ml. of a 20% solution of diisobutylaluminum hydride was added to a solution, cooled to -60°, of 150 mg. of (1S,5R,6R,7R)-6-[(E)-3,3-ethylenedioxy-4-(2-naphthyloxy)-1-butenyl]-7-(tetrahydropyran-2-yloxy)-2-oxabicyclo[3,3,0]octan-3-one (prepared according to Example 5[b]) in 15 ml. of absolute toluene. After 30 minutes, the mixture was combined with 0.75 ml. of isopropanol and 0.75 ml. of water and agitated for 30 minutes at 0°, diluted with 150 ml. of methylene chloride, filtered off from the precipitated aluminum compound, and evaporated under vacuum, thus obtaining 146 mg. of the title compound as a colorless oil. IR: 3600, 1630, 1600, 970 cm-1.

Workup

  1. customat -70°
  2. temperaturecooled to -60°, of 150 mg
  3. additiondiluted with 150 ml
  4. filtrationof methylene chloride, filtered off from the precipitated aluminum compound
  5. customevaporated under vacuum
  6. customthus obtaining 146 mg

Sources & evidence

ORD record
ord-30ac8176eb1d41258f3a56b5f124b7b5
Source dataset
uspto-grants-1978_05
Patent number
US04088775

Reaction notes

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