Lithium Hydroxide → [4-(5-tert-Butyl-4-isopropoxy-2-methyl-3-prop-2-ynyl-phenylethynyl)-phenyl]-acetic acid

HRID 1765866Notes

Reaction equation

HRID 1765866 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH2:27][C:28]#[C:29][Si](C)(C)C)[C:14]=2[CH3:34])=[CH:7][CH:6]=1.[OH-].[Li+]>CO.O1CCCC1>[C:19]([C:17]1[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH2:27][C:28]#[CH:29])[C:14]([CH3:34])=[C:13]([C:12]#[C:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:35])=[O:2])=[CH:10][CH:9]=2)[CH:18]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86600195{4-[5-Tert-butyl-4-isopropoxy-2-methyl-3-(3-trimethylsilanyl-prop-2-ynyl)-phenylethynyl]-phenyl}-acetic acid methyl ester

Product 1

HCID 57424262[4-(5-tert-Butyl-4-isopropoxy-2-methyl-3-prop-2-ynyl-phenylethynyl)-phenyl]-acetic acidYield 101.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {4-[5-tert-butyl-4-isopropoxy-2-methyl-3-(3-trimethylsilanyl-prop-2-ynyl)-phenylethynyl]-phenyl}-acetic acid methyl ester (Intermediate, 149, 0.038 g, 0.078 mmol) in methanol (1.5 mL) and tetrahydrofuran (1.5 mL) was treated with 2M lithium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at ambient temperature for 1.5 h. The volatiles were evaporated in vacuo to a residue that was neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product (0.032 g, 98%). 1H NMR (300 MHz, CDCl3): δ 7.50 (d, 2H, J=8.1 Hz), 7.43 (s, 1H), 7.27 (d, 2H, J=8.1 Hz), 4.82 (heptet, 1H, J=6.4 Hz), 3.67 (s, 2H), 3.48 (d, 2H, J=2.5 Hz), 2.58 (s, 3H), 1.39 (s, 9H), 1.28 (d, 6H, J=6.4 Hz).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo to a residue that
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-94af015859674ff399f4d879e083aeed
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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