Tetrabutylammonium Fluoride → HCID 69596295, compound

HRID 2212570Notes

Reaction equation

HRID 2212570 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:21][C:22](=[O:46])[C:23]([CH3:45])([CH3:44])[C:24]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:36][Si](C(C)(C)C)(C)C)[CH:32]=2)[CH:27]=1)=[O:25])[CH3:20]>C1COCC1.C(OCC)(=O)C>[CH2:19]([O:21][C:22](=[O:46])[C:23]([CH3:45])([CH3:44])[C:24]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([OH:36])[CH:32]=2)[CH:27]=1)=[O:25])[CH3:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69596330HCID 69596330, compound

Product 1

HCID 69596295HCID 69596295, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium floride 1M in THF (78 mL, 78 mmol) was added to a solution of 3-[6-(tert-butyl-dimethyl-silanyloxy)-naphthalen-2-yl]-2,2-dimethyl-3-oxo-propionic acid ethyl ester (77.1 mmol) in THF (300 mL) at room temperature for 0.5 h. The reaction was taken up in ethyl acetate, washed with water (2×) and brine, dried over magnesium sulfate, and concentrated to give the 3-(6-Hydroxy-naphthalen-2-yl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester as a crude oil.

Workup

  1. washwashed with water (2×) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-be48f4a8c89246979d9d795ff36f331d
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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