Sodium Bicarbonate → HCID 118027235, compound

HRID 926178Notes

Reaction equation

HRID 926178 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]=[CH:17][C:18]=2[CH3:23])[C:13]=1[O:24]S(C)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[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]=[CH:17][C:18]=2[CH3:23])[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 89681748HCID 89681748, compound

Product 1

HCID 118027235HCID 118027235, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(3,5-dimethyl-1-(methylsulfonyloxy)naphthalen-2-yl)acetate (0.19 g, 0.48 mmol) in THF (3 mL) cooled to 0° C. was treated with tetrabutylammonium fluoride (1M in THF, 1.4 mL, 1.4 mmol). After 1 hour, saturated NaHCO3 was added and the aqueous layer extracted with EtOAc. The combined organics are washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification via Yamazen column chromatography afforded (S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,5-dimethylnaphthalen-2-yl)acetate that is contaminated with a small percentage of an inseparable, uncharacterized side product. 1H-NMR: 400 MHz, (CDCl3) δ: 8.96 (s, 1H); 8.13 (obs m, 1H); 7.30 (obs m, 2H); 5.51 (s, 1H); 4.23-4.05 (m, 2H); 2.62 (br s, 6H); 1.31 (s, 9H); 1.19 (t, J=7.2 Hz, 3H).

Workup

  1. extractionthe aqueous layer extracted with EtOAc
  2. washThe combined organics are washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via Yamazen column chromatography

Sources & evidence

ORD record
ord-a35b4d857126455a894e94d0bd58c6fd
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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