Selectfluor → (S)-ethyl 2-tert-butoxy-2-(4-fluoro-1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate

HRID 926175Notes

Reaction equation

HRID 926175 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:26].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[C:20]([F:26])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 89681728(S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate

Product 1

HCID 89681746(S)-ethyl 2-tert-butoxy-2-(4-fluoro-1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate (0.62 g, 1.9 mmol) in MeCN (14 mL) cooled to 0° C. was treated with SelectFluor® fluorinating reagent (0.66 g, 1.9 mmol). The cold bath was removed and after 90 minutes the reaction was quenched with pH 7 buffer solution. The aqueous layer was extracted with EtOAc and the combined organics washed with brine and dried over anhydrous MgSO4 and filtered. Following concentration in vacuo, the desired product was obtained via silica gel chromatography followed by preparatory HPLC to afford (S)-ethyl 2-tert-butoxy-2-(4-fluoro-1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate. LCMS-ESI− (m/z): [M−H]− calcd for C20H24O4F: 347.4. found: 347.2.

Workup

  1. customThe cold bath was removed and after 90 minutes the reaction
  2. customwas quenched with pH 7 buffer solution
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organics washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-37520dd1b0b54a7c8afd6acd61576c46
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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