Methanol → HCID 57804225, compound

HRID 2102891Notes

Reaction equation

HRID 2102891 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=2[C:21]#[C:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:13]([O:15]CC)=[O:14])[CH2:3][CH2:2]1.CO>O>[CH3:24][C:23]([CH3:26])([CH3:25])[C:22]#[C:21][C:20]1[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:9][CH2:8][CH2:7][N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 57804094HCID 57804094, compound

Product 1

HCID 57804225HCID 57804225, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 3-(2-morpholinoethoxy)-4-(3,3-dimethylbut-1-ynyl)benzoate (0.34 g, 0.95 mmol) and LIOH (68 mg, 2.84 mmol) were placed in a 3:1 mixture of methanol:water (30 mL) and heated at 60° C. for 3.5 h. The reaction was cooled and concentrated in vacuo to a volume of 20 mL. The mixture was 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 a vacuum oven to give the product (0.24 g, 70%) as a solid. m/z=330.1 (M−1).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo to a volume of 20 mL
  3. customThe mixture was placed 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 a vacuum oven

Sources & evidence

ORD record
ord-dbbdd476a60b4245964b1a6b26273e85
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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