Tetrabutylammonium Fluoride → (3-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

HRID 2384004Notes

Reaction equation

HRID 2384004 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[C:11]([O:20]S(C(F)(F)F)(=O)=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O.Cl>[C:1]([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[C:11]([OH:20])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59192506HCID 59192506, compound

Product 1

HCID 59192505(3-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl esterYield 85%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (5-oxo-3-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (XXIX, 140 mg, 0.33 mmol) in tetrahydrofuran (5 mL) was added a 1.0 M solution of tetrabutylammonium fluoride (660 μL, 0.66 mmol) in tetrahydrofuran at room temperature under nitrogen. The resulting light yellow solution was stirred for 5 h at room temperature, and then diluted with water (10 mL) and 1.0N hydrochloric acid (5 mL). The mixture was extracted with ethyl acetate (2×35 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by ISCO (40 g) column chromatography (gradient elution with 5-50% ethyl acetate in hexanes) to provide (3-hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (82 mg, 85%) as a yellow solid: ES(+)-HRMS m/e calcd. for C16H20O5 (M+H)+293.1384, obsd. 293.1383.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×35 mL)
  2. washThe combined organic extracts were washed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by ISCO (40 g) column chromatography (gradient elution with 5-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-57439a661e2f4e1e9c20535913581d8a
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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