TBAF tetrahydrofuran → HCID 57414919, compound

HRID 1908900Notes

Reaction equation

HRID 1908900 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]3[CH:37]=[CH:36][C:27]4[C@H:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:29][O:30][C:26]=4[CH:25]=3)[CH:17]=2)=[C:11]([CH3:38])[C:10]=1[Cl:39])(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:39][C:10]1[C:11]([CH3:38])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]3[CH:37]=[CH:36][C:27]4[C@H:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:29][O:30][C:26]=4[CH:25]=3)[CH:17]=2)[C:13]([CH3:15])=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 59342562HCID 59342562, compound

Product 1

HCID 57414919HCID 57414919, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl {(3S)-6-[(4′-{[tert-butyl(dimethyl)silyl]oxy}-3′-chloro-2′,6′-dimethylbiphenyl-3-yl)methoxy]-2,3-dihydro-1-benzofuran-3-yl}acetate (2.01 g, 3.54 mmol) in tetrahydrofuran (20 mL) was added 1 M tetrabutylammonium fluoride tetrahydrofuran solution (3.9 mL, 3.9 mmol) at room temperature, and the mixture was stirred at the same temperature for 3 hr under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50) to give the title compound (1.41 g, yield 88%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50)

Sources & evidence

ORD record
ord-604bd94438d94c40a156d8edad96c82c
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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