Acetic Acid → HCID 59841576, compound

HRID 1894683Notes

Reaction equation

HRID 1894683 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:17][CH:16]2C([O-])=O)=[CH:11][CH:10]=1.[Na+].C1(C)C=CC=CC=1.O.C(O)(=O)C>C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1140TolueneHCID 86624480HCID 86624480, compound

Product 1

HCID 59841576HCID 59841576, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
73 °C

Procedure

A mixture of sodium 3-(4-(pyridin-2-yloxymethyl)-phenyl)-oxiran-2-carboxylate (9.95 g) described in Manufacturing Example 1-3-2, toluene (200 mL), water (120 mL), and acetic acid (16 mL) was stirred for 90 minutes at 73° C. The reaction mixture was cooled to room temperature, ethyl acetate was added to the reaction mixture for extraction, and the organic layer was separated, washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure to obtain the title compound (6.82 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-170645b4618843e2bcd999b3e70cb85b
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

Loading…