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

HRID 1585860
Notes
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Reaction equation

HRID 1585860 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-255cd9e06f5044e98349a308ecd5585c
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05939570

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes