Methanol → HCID 57804125, compound

HRID 2102903Notes

Reaction equation

HRID 2102903 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][C:7]=2[O:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:3][CH2:2]1.[Li+].[OH-].CO>O>[CH:1]1([C:4]#[C:5][C:6]2[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=2[O:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 57804112HCID 57804112, compound

Product 1

HCID 57804125HCID 57804125, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-(2-cyclopropylethynyl)-3-(cyclopropylmethoxy)benzoate (0.47 g, 1.65 mmol) and LiOH (120 mg, 4.96 mmol) were placed in a 3:1 mixture of methanol:water (50 mL) and heated at 60° C. for 3.5 h. The reaction was cooled and concentrated in vacuo to a volume of 20 mL, then placed in an ice-water bath and acidified to pH 5 with conc. HCl. A white solid precipitated which was filtered and washed thoroughly with water. The solid was dried in the vacuum oven to give the product (0.44 g, 98%). m/z=257.1 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo to a volume of 20 mL
  3. customplaced in an ice-water bath
  4. customA white solid precipitated which
  5. filtrationwas filtered
  6. washwashed thoroughly with water
  7. customThe solid was dried in the vacuum oven

Sources & evidence

ORD record
ord-05c0e188ced249bfa4edb788f7009633
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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