Diethyl Ether → HCID 131718407, compound

HRID 1033777Notes

Reaction equation

HRID 1033777 reaction equation
[H-].[CH2:2]([Al+]C[CH:8]([CH3:10])[CH3:9])[CH:3](C)[CH3:4].C(Cl)Cl.CCO[CH2:17][CH3:18].[C@H:19](O)([C:25]([O-])=O)[C@@H:20](O)[C:21]([O-])=[O:22].[Na+].[K+]>>[CH:21]([OH:22])=[CH:20][CH2:19][CH2:25][CH2:10][CH2:8][CH3:9].[CH2:18]1[CH2:17][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 9357Potassium Sodium TartrateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 131718407HCID 131718407, compoundYield 70%

Conditions

Temperature
0 °C

Procedure

A 1.0M solution of diisobutylaluminum hydride in methylene chloride (3.3 ml, 3.3 mmol) was added at 0° C. to the tris (THP) ether (687 mg, 1.11 mmol) obtained above. The resulting solution was stirred at 0° C. for 2 h and worked up by the addition of a saturated solution of Rochelle salt. The mixture was extracted three times with ethyl acetate The organic extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated to give 578 mg of crude product which was chromatographed over silica gel (30-40% EtOAc in hexane) to give 454 mg (70% yield) of pure tris (THP) ether of cyclopentane heptenol, 5-cis-2(3-αhydroxy-1-trans octenyl)-3,5-dihydroxy, [1α,2β,3α,5α].

Workup

  1. customobtained above
  2. extractionThe mixture was extracted three times with ethyl acetate The
  3. extractionorganic extract
  4. washwas washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give 578 mg of crude product which
  8. customwas chromatographed over silica gel (30-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-0e8d10029e91451a8652603b2b1b1709
Source dataset
uspto-grants-1994_05
Patent number
US05312842

Reaction notes

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