Acetic Acid → (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-vinylnaphthalen-2-yl)acetic acid

HRID 514025Notes

Reaction equation

HRID 514025 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH:22]=[CH2:23])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CC(O)=O>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH:22]=[CH2:23])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 68086079(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-vinylnaphthalen-2-yl)acetate

Product 1

HCID 56602125(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-vinylnaphthalen-2-yl)acetic acidYield 76.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-vinylnaphthalen-2-yl)acetate (7.4 mg, 0.0175 mmol) in THF/MeOH (1/1, 1 mL), was added NaOH (2 N, 280 L). The reaction mixture was stirred at room temperature overnight. Then the temperature was raised to 40° C. and the reaction mixture was stirred for 4 h. The reaction was then cooled down and neutralized by adding HOAc. The reaction mixture was concentrated in vacuo and the residue was purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to provide 5.3 mg of the desired product. 1H-NMR: 400 MHz, (CD3OD) δ: 8.07 (s, 1H), 7.89 (d, J=4.0 Hz, 1H), 7.60-7.54 (m, 4H), 7.48-7.44 (m, 1H), 7.35-7.31 (m, 2H), 7.25-7.22 (m, 1H), 5.76-5.71 (m, 1H), 5.29-5.26 (m, 1H), 5.21 (s, 1H), 0.98 (s, 9H). LCMS-ESI− (m/z): [M−H]− calcd for C24H23ClO3: 393.1. Found: 393.0.

Workup

  1. temperatureThen the temperature was raised to 40° C.
  2. stirringthe reaction mixture was stirred for 4 h
  3. temperatureThe reaction was then cooled down
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-4e2d6f41306d4ef58c2c4f7fe168333d
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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