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Sodium Sulfate → 17-Methylenestr-4-en-3beta-ol

HRID 1781945
Notes
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Reaction equation

HRID 1781945 reaction equation
C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[CH2:18]=[C:19]1[CH2:24][CH2:23][C@H:22]2[C@H:25]3[C@H:34]([CH2:35][CH2:36][C@:20]12[CH3:21])[C@@H:33]1[C:28](=[CH:29][C:30](=[O:37])[CH2:31][CH2:32]1)[CH2:27][CH2:26]3.[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH2:18]=[C:19]1[CH2:24][CH2:23][C@H:22]2[C@H:25]3[C@H:34]([CH2:35][CH2:36][C@:20]12[CH3:21])[C@@H:33]1[C:28](=[CH:29][C@@H:30]([OH:37])[CH2:31][CH2:32]1)[CH2:27][CH2:26]3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 1587099217-Methyleneestra-4-EN-3-oneHCID 16684435Lithium tritertbutoxyaluminohydride

Product 1

HCID 2287306917-Methylenestr-4-en-3beta-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium tri-t-butoxyaluminohydride (766.6 mg, 3.015 mmol) was added to a solution of 17-methylenestr-4-en-3-one (16, 203.7 mg, 0.7533 mmol) in 10 mL of anh. ether and the reaction was stirred 4 h. See FIG. 18. Glauber's salt (3.80 g) was added and the suspension was stirred an additional 1/2 h. The mixture was filtered through diatomaceous earth and the residue was washed five times with 10 mL portions of ether. The combined filtrates were concentrated under reduced pressure and then subjected to preparative TLC (5% ethyl acetate/methylene chloride on silica gel GF, 1000μ thickness) to give white needles (60.2 mg. 0.221 mmol, 29%) homogeneous to TLC (Rf 0.37, 5% ethyl acetate/methylene chloride on silica gel). (NA-1994A-282)

Workup

  1. stirringthe suspension was stirred an additional 1/2 h
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washthe residue was washed five times with 10 mL portions of ether
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customto give white needles (60.2 mg. 0.221 mmol, 29%) homogeneous to TLC (Rf 0.37, 5% ethyl acetate/methylene chloride on silica gel)

Sources & evidence

ORD record
ord-95307c0c52d74de4a0f61e340d47b4aa
Source dataset
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05633392

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes