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TBAF tetrahydrofuran → 20-(2-Ethyl-2-hydroxybutoxy)-1alpha,3beta-dihydroxy-20-methylpregna-5,7,16-triene

HRID 1792197
Notes
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Reaction equation

HRID 1792197 reaction equation
[Si]([O:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][C:26]([CH2:30][CH3:31])([OH:29])[CH2:27][CH3:28])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:39][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:27]([C:26]([OH:29])([CH2:30][CH3:31])[CH2:25][O:24][C:21]([CH3:23])([C:20]1[C@:32]2([CH3:38])[C@H:17]([C:16]3[C@H:35]([CH2:34][CH2:33]2)[C@:36]2([CH3:37])[C:13]([CH2:12][C@@H:11]([OH:39])[CH2:10][C@@H:9]2[OH:8])=[CH:14][CH:15]=3)[CH2:18][CH:19]=1)[CH3:22])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 696301181alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-(2-ethyl-2-hydroxybutoxy)-20-methylpregna-5,7,16-triene

Product 1

HCID 6963022620-(2-Ethyl-2-hydroxybutoxy)-1alpha,3beta-dihydroxy-20-methylpregna-5,7,16-trieneYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(2-ethyl-2-hydroxybutoxy)-20-methylpregna-5,7,16-triene (32.0 mg, 0.0475 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (0.3 ml, 0.3 mmol) and tetrahydrofuran (0.5 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under heating for 16 hours), worked up and the thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), hexane:ethyl acetate:ethanol=10:5:1, developed twice) to give the titled compound (19.8 mg, 94%) as a colorless oil.

Workup

  1. temperatureof Example 5(2) (reflux under heating for 16 hours)
  2. customthe thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), hexane

Sources & evidence

ORD record
ord-119241f1e30f4606852a9293fbdb4883
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074777B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes