Trimethylsilyl iodide → Methyl 5-tert-butyl-6-hydroxy-4'-methyl-3-biphenylcarboxylate

HRID 2377203Notes

Reaction equation

HRID 2377203 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22]([O:24][CH3:25])=[O:23])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])C1C=CC=CC=1.C[Si](I)(C)C>C(#N)C>[C:26]([C:10]1[CH:11]=[C:12]([C:22]([O:24][CH3:25])=[O:23])[CH:13]=[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:9]=1[OH:8])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 12084817Methyl 6-benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarboxylate

Product 1

HCID 12084822Methyl 5-tert-butyl-6-hydroxy-4'-methyl-3-biphenylcarboxylateYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

5.4 g (14 mmol) of methyl 6-benzyloxy-5-tert-butyl-4′-methyl-3-biphenylcarboxylate (Example 1, d) are dissolved in 100 mL of acetonitrile. 6 mL (41 mmol) of trimethylsilyl iodide are added and the mixture is heated at 50° C. for 24 hours. After extraction, the residue obtained is subjected to esterification conditions similar to those of Example 1 b, and the residue obtained is purified by chromatography. A white solid is obtained (m=1.6 g, yield=36%; m.p.=105° C.).

Workup

  1. extractionAfter extraction
  2. customthe residue obtained
  3. customthe residue obtained
  4. customis purified by chromatography
  5. customA white solid is obtained (m=1.6 g, yield=36%; m.p.=105° C.)

Sources & evidence

ORD record
ord-350307f600c54d5bae5d5afcc5fad76e
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

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