Ethyl Acetate → HCID 23670208, compound

HRID 1829078Notes

Reaction equation

HRID 1829078 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]([CH2:21][C:22]([OH:24])=[O:23])[O:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C[O-].[Na+:27].CO.CCOC(C)=O>CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12]3\[O:13][CH:14]([CH2:21][C:22]([O-:24])=[O:23])[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]\3=4)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Na+:27]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23694274Sodium methanolate methanolHCID 69659264HCID 69659264, compound

Product 1

HCID 23670208HCID 23670208, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a slurry of [3-(6-fluoro-2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid (521 mg, 1.60 mmol) in MeOH (100.0 ml) at room temperature was added 0.5M NaOMe/MeOH (3.20 ml). The solution was rapidly stirred for 15 minutes and then rotary evaporated (combined 16 mg of product obtained from previously run reaction). The solid was chased with MeOH (20 ml) and then EtOAc (15 ml) to give sodium [(3E)-3-(6-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1,3-dihydro-2-benzofuran-1-yl]acetate as a yellow solid (557 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-c03acb13ec2d4e7ea8b43f384e0dd9f9
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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