Tetrabutylammonium Fluoride → ethyl (1S,1aS,6bR)-5-hydroxy-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylate

HRID 920113Notes

Reaction equation

HRID 920113 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:21][C:22]([C@H:24]1[C@H:29]2[C@@H:25]1[O:26][C:27]1[CH:33]=[CH:32][C:31]([O:34][Si](C(C)(C)C)(C)C)=[CH:30][C:28]=12)=[O:23])[CH3:20]>C1COCC1>[OH:34][C:31]1[CH:32]=[CH:33][C:27]2[O:26][C@@H:25]3[C@@H:24]([C:22]([O:21][CH2:19][CH3:20])=[O:23])[C@@H:29]3[C:28]=2[CH:30]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131734886(1S,1aS,6bR)-Ethyl-5-((tert-butyldimethylsilyl)oxy)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylate

Product 1

HCID 89670235ethyl (1S,1aS,6bR)-5-hydroxy-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetra-n-butylammonium fluoride (TBAF, 1M in THF, 4 mmol) was added dropwise to a solution of the product of Step A (7.3 g, crude) in THF (100 mL) at 0° C. The reaction was stirred at RT for 30 min. The mixture was concentrated and purified by column chromatography to afford the title compound as a solid (2.52 g, 57% for 2 steps, 72% ee).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-a5a525f98fb04440b06e8e4a11ea08db
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Reaction notes

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