Methyl iodide → HCID 70375164, compound

HRID 580239Notes

Reaction equation

HRID 580239 reaction equation
[CH3:1][O:2][C:3]1[C:20]([O:21][CH3:22])=C(OC)C(OC)=[C:17](C)[C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.C([N-][CH:32]([CH3:34])[CH3:33])(C)C.[Li+].[O:36]1[CH2:40]CCC1.CCCCCC.CI.[O:49]1CCC[CH2:50]1.[CH3:54]N(C)P(N(C)C)(N(C)C)=O>>[CH3:1][O:2][C:3]1[C:4](=[CH:17][C:32]([O:36][CH3:40])([CH3:33])[CH:34]([O:49][CH3:50])[C:20]=1[O:21][CH3:22])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([CH3:54])[C:14]([OH:16])=[O:15])=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 14852328HCID 14852328, compoundHCID 21883165Tetrahydrofuran hexaneHCID 86583969tetrahydrofuran HMPA

Product 1

HCID 70375164HCID 70375164, compound

Procedure

4-(2,3,4,5-Tetramethoxy-6-methylbenzyloxy)phenylacetic acid (2.07 g, 5.5 mmol) was dissolved in tetrahydrofuran-hexamethylphosphoramide (10:1, 11 ml). A solution of lithium diisopropylamide in tetrahydrofuran-hexane (20 ml, 2 equivalents) was cooled to -20° C. and the above-mentioned solution was added to this solution. The mixture was stirred for 30 minutes and then, after addition of methyl iodide (0.85 g, 60 mmol), it was stirred for 1.5 hours, while the reaction temperature was gradually raised from -20° C. to 0° C. After completion of the reaction, extraction and isolation conducted in a conventional manner gave 2-[4-(2,3,4,5-tetramethoxy-5-methylbenzyloxy)phenyl]propionic acid (Compound 19).

Workup

  1. additionthe above-mentioned solution was added to this solution
  2. stirringwas stirred for 1.5 hours, while the reaction temperature
  3. temperaturewas gradually raised from -20° C. to 0° C
  4. customAfter completion of the reaction, extraction and isolation

Sources & evidence

ORD record
ord-e12b074bb755456ca6a3bbaecf19dbe2
Source dataset
uspto-grants-1988_06
Patent number
US04751303

Reaction notes

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