Ethyl Acetate → HCID 19887970, compound

HRID 231201Notes

Reaction equation

HRID 231201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)[C:14]2=[O:30])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:29][O:28][C:20]1[CH:19]=[C:18]([CH:15]2[CH2:16][CH2:17][CH:13]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[CH:14]2[OH:30])[CH:23]=[C:22]([O:24][CH3:25])[C:21]=1[O:26][CH3:27]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19887978HCID 19887978, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19887970HCID 19887970, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2.26 g of the compound of Example 2 in 54 ml of tetrahydrofuran which was cooled to -78° C. was added 14.5 ml of a 1.5M solution of diisobutylaluminum hydride in toluene. The reaction mixture was then stirred for 2 hours, while maintaining the temperature at -78° C., after which time it was warmed to room temperature. The mixture was then stirred for an additional 22 hours, after which time it was poured into a mixture of 100 ml of ethyl acetate and 100 ml of a saturated aqueous ammonium chloride solution. The resultant mixture was then filtered through Celite and the filtrate was extracted with a mixture of ethyl acetate and water. The organic layers were then combined, dried and evaporated to afford the crude residue which was chromatographed on silica gel employing a mixture of hexane and isopropyl alcohol in a ratio of 3:1 as the eluent to yield the 1α, 2α, 5β and 1α, 2α, 5α isomers of the title compound, the former of which had a m.p. of 126°-128° C., and the latter of which had a m.p. of 138°-140° C.

Workup

  1. temperatureafter which time it was warmed to room temperature
  2. stirringThe mixture was then stirred for an additional 22 hours
  3. filtrationThe resultant mixture was then filtered through Celite
  4. extractionthe filtrate was extracted with a mixture of ethyl acetate and water
  5. customdried
  6. customevaporated
  7. customto afford the crude residue which
  8. customwas chromatographed on silica gel employing
  9. additiona mixture of hexane and isopropyl alcohol in a ratio of 3:1 as the eluent

Sources & evidence

ORD record
ord-81b44794c0b7483c911b889e3bbda7bb
Source dataset
uspto-grants-1989_07
Patent number
US04845129

Reaction notes

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