Lithium Hydroxide → HCID 58883461, compound

HRID 1869986Notes

Reaction equation

HRID 1869986 reaction equation
[CH:1]([O:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[C:16]([F:26])[CH:15]=2)[CH:7]=1)([CH3:3])[CH3:2].[OH-].[Li+]>C(O)(C)C.O1CCCC1>[CH:1]([O:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[C:16]([F:26])[CH:15]=2)[CH:7]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69070551HCID 69070551, compound2×

Product 1

HCID 58883461HCID 58883461, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-ethoxycarbonylmethyl-3-fluoro-phenylethynyl)-benzoic acid isopropyl ester (Intermediate 138, 0.1 g, 0.27 mmol) in isopropanol (2 mL) and tetrahydrofuran (2 mL) was treated with a 2M solution of lithium hydroxide (1 mL, 2 mmol). After 40 min. at ambient temperature, the reaction mixture was concentrated in vacuo a bit, neutralized with 10% hydrochloric acid and the solid formed was filtered, washed with water and dried to afford the title compound (0.09 g, 97%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo a bit
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5f249f350ac14fbdb751257c630190cd
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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