Ethyl Acetate → HCID 23672261, compound

HRID 1829077Notes

Reaction equation

HRID 1829077 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20][C:21]([OH:23])=[O:22])[O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C[O-].[Na+:26].CO.CCOC(C)=O>CO>[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[C:11]1\[O:12][CH:13]([CH2:20][C:21]([O-:23])=[O:22])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]\1=3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Na+:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23694274Sodium methanolate methanolHCID 69659233HCID 69659233, compound

Product 1

HCID 23672261HCID 23672261, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a slurry of [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid (430 mg, 1.40 mmol) in MeOH (100.0 ml) at room temperature was added 0.5M NaOMe/MeOH (2.80 ml). The solution was rapidly stirred for 15 minutes and then rotary evaporated (combined 116 mg of product obtained from previously run reaction). The solid was chased with MeOH (20 ml), and then with EtOAc (2×15 ml) to give sodium [(3E)-3-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1,3-dihydro-2-benzofuran-1-yl]acetate as a yellow solid (576 mg, 100%).

Workup

  1. customrotary evaporated (
  2. customobtained from previously run reaction)

Sources & evidence

ORD record
ord-42ed980e13324e8ca2712ad91a1ebf42
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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