Lithium Hydroxide → HCID 56602323, compound

HRID 514044Notes

Reaction equation

HRID 514044 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:30])[C:6]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=[C:7]2[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[OH-].[Li+]>O1CCCC1.C(O)C.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:30])[C:6]([CH:19]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C:20]([OH:22])=[O:21])=[C:7]2[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67126073HCID 67126073, compound

Product 1

HCID 56602323HCID 56602323, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-(5-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (30 mg, 0.061 mmol) in tetrahydrofuran:ethanol:water (2:2:1, 3 mL) was added lithium hydroxide (7 mg, 0.31 mmol) and the reaction was heated to 50° C. overnight. Crude reaction purified by reverse phase HPLC (Gemini, 40-100% ACN/H2O+0.1% TFA). Product lyophilized to give a white powder (5.9 mg). 1H-NMR: 400 MHz, (CD3OD) δ: 8.07 (s, 1H), 7.77 (d, J=6.0 Hz, 1H), 7.58 (s, 2H), 7.55 (as, 1H), 7.32 (d, J=8.8 Hz, 1H), 7.26 (d, J=8.8 Hz, 1H), 7.18 (m, 1H), 5.17 (s, 1H), 2.67 (s, 3H), 0.99 (s, 9H). LCMS-ESI− (m/z): [M−H]− calcd for C23H21BrClO3: 460.8. found; 460.2.

Workup

  1. customCrude reaction
  2. custompurified by reverse phase HPLC (Gemini, 40-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-34ed566fd55e492e99e740c5630c47fc
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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