Water → HCID 69465704, compound

HRID 968189Notes

Reaction equation

HRID 968189 reaction equation
[F:1][C:2]1[C:3]([O:20]C)=[CH:4][C:5]2[CH2:6][CH2:7][C@H:8]3[C@H:16]4[C@@H:12]([C@@H:13]([OH:17])[CH2:14][CH2:15]4)[CH2:11][CH2:10][C@@H:9]3[C:18]=2[CH:19]=1.CC(C[AlH]CC(C)C)C.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]2[CH2:6][CH2:7][C@H:8]3[C@H:16]4[C@@H:12]([CH:13]([OH:17])[CH2:14][CH2:15]4)[CH2:11][CH2:10][C@@H:9]3[C:18]=2[CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 15513570HCID 15513570, compound

Product 1

HCID 69465704HCID 69465704, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The solution of 0.53 g of 2-fluoro-3-methoxy-gona-1,3,5(10)-trien-17β-ol in 50 ml of toluene is mixed with 5 ml of 20% solution of DIBAH in toluene and heated for 2 hours to 80° C. After cooling, water is added drop by drop until the reaction has run its course, then it is dispersed between water and ethyl acetate, the ethyl acetate phase is washed with concentrated common salt solution and dried with sodium sulfate. After evaporation, a residue remains that is chromatographed on silica gel with hexane-ethyl acetate, and the yield is 0.32 g (63% of theory).

Workup

  1. temperatureheated for 2 hours to 80° C
  2. temperatureAfter cooling
  3. washthe ethyl acetate phase is washed
  4. concentrationwith concentrated common salt solution
  5. dry with materialdried with sodium sulfate
  6. customAfter evaporation
  7. customthat is chromatographed on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-e90ec70e2c0142f399bcd3e4e3ee1def
Source dataset
uspto-grants-2005_10
Patent number
US06958327B1

Reaction notes

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