Sodium Bicarbonate → (S)-ethyl 2-(5-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

HRID 926176Notes

Reaction equation

HRID 926176 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:31])[C:6]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]2[O:12]S(C(F)(F)F)(=O)=O.C(O[C@@H](C1C(C)=CC2C(=CC=C(C)C=2)C=1OS(C(F)(F)F)(=O)=O)C(OCC)=O)(C)(C)C.BrC1C=CC=CC=1CC(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:31])[C:6]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]2[OH:12]

Participants

8

Reactant 5

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 27340921-(2-Bromophenyl)propan-2-oneHCID 89681723(S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetateHCID 89681749(S)-ethyl 2-(5-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 89681750(S)-ethyl 2-(5-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (S)-ethyl 2-(5-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (0.90 g, 1.7 mmol; prepared in a similar fashion to (S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate beginning with 1-(2-bromophenyl)propan-2-one) in THF (7 mL) cooled to 0° C. was treated with tetrabutylammonium fluoride (1M in THF, 1.7 mL, 1.7 mmol) dropwise. After 1 hour, saturated NaHCO3 and EtOAc were added and the aqueous layer extracted with EtOAc. The combined organics were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification via Yamazen column chromatography (0-15% EtOAc/hex) afforded (S)-ethyl 2-(5-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate. LCMS-ESI− (m/z): [M−H]− calcd for C19H22O4Br: 395.07. found: 395.04.

Workup

  1. extractionthe aqueous layer extracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via Yamazen column chromatography (0-15% EtOAc/hex)

Sources & evidence

ORD record
ord-7500c315cbe643faae34b7e1500e5ff0
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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