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

HRID 275686
Notes
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Reaction equation

HRID 275686 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 ½ 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).

Workup

  1. stirringthe suspension was stirred an additional ½ 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-2a97a162a68c41cbb41fb76f68087d37
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06352980B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes