Sodium sulfate decahydrate → Estra-4,16-dien-3-ol

HRID 1604745Notes

Reaction equation

HRID 1604745 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][C:12](=[O:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][CH:12]([OH:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 15870982Estra-4,16-dien-3-one2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 54095959Estra-4,16-dien-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To estra-4,16-dien-3-one, (1) (87.2 mg, 0.340 mmol) in 1.7 mL of anh. ether was added lithium aluminum hydride (15.0 mg, 0.395 mmol) and the suspension was stirred 17 min. Reaction was then agitated 10 min. with 0.50 g of sodium sulfate decahydrate and filtered through Celite. The residue was washed with three 10 mL portions of ether and the combined filtrates were concentrated under reduced pressure. Preparative TLC (5% ethyl acetate/dichloro-methane on silica gel) gave crude product (50.0 mg) as a yellow resin. This could be rechromatographed until sufficiently pure.

Workup

  1. customReaction
  2. filtrationfiltered through Celite
  3. washThe residue was washed with three 10 mL portions of ether
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-3409bc8121294fc3856b349d317e76ce
Source dataset
uspto-grants-1999_11
Patent number
US05994568

Reaction notes

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