Lithium Hydroxide → HCID 56602523, compound

HRID 514048Notes

Reaction equation

[C:1]([O:5][CH: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[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-].[Li+]>O1CCCC1.C(O)C.O>[C:1]([O:5][CH: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[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,5-dimethylnaphthalen-2-yl)acetate (32 mg, 0.075 mmol) in tetrahydrofuran: ethanol:water (2:2:1, 3 mL) was added lithium hydroxide (9 mg, 0.377 mmol) and the reaction was heated to 50° C. overnight. The reaction was purified by reverse phase HPLC (Gemini, 40-100% ACN/H2O+0.1% TFA). The product was lyophilized to give a white powder (16.8 mg). 1H-NMR: 400 MHz, (CD3OD) δ: 7.86 (s, 1H), 7.54 (m, 3H), 7.29 (m, 2H), 7.16 (t, J=8.8 Hz, 1H), 7.08 (d, J=8.8 Hz, 1H), 5.17 (s, 1H), 2.69 (s, 3H), 2.65 (s, 3H), 0.98 (s, 9H). LCMS-ESI− (m/z): [M−H]− calcd for C24H24ClO3: 395.15; found: 394.97.

Workup

customThe reaction was purified by reverse phase HPLC (Gemini, 40-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record: ord-d337dfcc3b7f41fab45227834d945507
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

Loading…