TBAF tetrahydrofuran → HCID 59714886, compound

HRID 2223915Notes

Reaction equation

HRID 2223915 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([O-:34])=[O:33])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].[CH2:40]([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O1CCCC1>[OH:1][CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([O:34][CH3:40])=[O:33])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 86760672HCID 86760672, compound

Product 1

HCID 59714886HCID 59714886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]benzoate (synthesized in Example 35) (547 mg) in tetrahydrofuran (4 mL) was added a 1M tetrabutyl ammonium fluoride/tetrahydrofuran solution (1 mL) at room temperature. The solution was then stirred for 2 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (2:1)] to give the title compound (226 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-84b05191a8cf407996706db07e152a89
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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