Trimethylsilyl iodide → HCID 20138901, compound

HRID 1905750Notes

Reaction equation

HRID 1905750 reaction equation
C[Si](I)(C)C.C[O:7][C:8]1[CH:9]=[C:10]2[C:13]([CH3:22])([C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH2:12][C:11]2=[CH:23][CH:24]=1>C(Cl)Cl>[OH:7][C:8]1[CH:9]=[C:10]2[C:13]([CH3:22])([C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH2:12][C:11]2=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 20138929HCID 20138929, compound

Product 1

HCID 20138901HCID 20138901, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyliodide (46.4 ml) is added dropwise to a stirred solution of the 5-methoxy compound of Step 3. above (42.1 g) in methylene chloride (100 ml) under nitrogen and the mixture is refluxed for 48 hours. The reaction mixture is diluted with methylene chloride, washed with 10% aq. sodium sulphite, water, dried, filtered, and evaporated in vacuo. The residue is triturated with acetonitrile affording a white solid. The filtrate is evaporated in vacuo affording a viscous liquid which is chromatographed on silica gel. The purified fractions are washed with sat'd sodium bicarbonate, sat'd sodium chloride, dried, filtered and evaporated in vacuo affording the desired product as a yellow solid.

Workup

  1. washwashed with 10% aq. sodium sulphite, water
  2. customdried
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue is triturated with acetonitrile affording a white solid
  6. customThe filtrate is evaporated in vacuo
  7. customaffording a viscous liquid which
  8. customis chromatographed on silica gel
  9. washThe purified fractions are washed with sat'd sodium bicarbonate
  10. customdried
  11. filtrationfiltered
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-85274739ca1c424eb02a93b17bab366d
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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