Sodium Sulfate → HCID 15463285, compound

HRID 2270539Notes

Reaction equation

HRID 2270539 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[C:8]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[C:17](=O)[CH2:16]3)[CH2:13][CH2:12]1)=CC.[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:8][C@H:11]1[CH2:12][CH2:13][C@H:14]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:28]12[CH3:29])[C@:23]1([CH3:24])[C:18](=[CH:19][CH:20]([OH:30])[CH2:21][CH2:22]1)[CH2:17][CH2:16]3

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 53668100HCID 53668100, compound

Product 1

HCID 15463285HCID 15463285, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Refer to FIG. 189. LAH (21.3 mg, 0.561 mmol) was added to a solution of 17β-methylandrost-4-en-3-one (7, 143.2 mg, 0.4999 mmol) (J. B. Jones and K. D. Gordon, Can. Chem. 1972, 50, 2712-2718) in 2.8 ml of anh. ether. After stirring the suspension for 30 min. Glauber's salt (0.76 g) was added and the mixture stirred a further ½ h. Ether (10 ml) was added and the suspension was filtered through diatomaceous earth. The residue was washed with three 10 ml portions of ether and the combined filtrates were concentrated under reduced pressure. The crude product was separated by preparative TLC (silica gel GF, 1000μ, 5% ethyl acetate/methylene chloride as eluent) into a more polar component (Rf 0.30, 77.9 mg, 0.270 mmol, 54%) and a less polar component (Rf 10 0.43, 10.3 mg, 0.0357 mmol, 7%).

Workup

  1. stirringthe mixture stirred a further ½ h
  2. filtrationthe suspension was filtered through diatomaceous earth
  3. washThe residue was washed with three 10 ml portions of ether
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customThe crude product was separated by preparative TLC (silica gel GF, 1000μ, 5% ethyl acetate/methylene chloride as eluent) into a more polar component (Rf 0.30, 77.9 mg, 0.270 mmol, 54%)

Sources & evidence

ORD record
ord-62804596e226444ba014244d738648cb
Source dataset
uspto-grants-2001_12
Patent number
US06331534B1

Reaction notes

Loading…