Triethylamine → HCID 131724410, compound

HRID 2085735Notes

Reaction equation

HRID 2085735 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](I)=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([O:24][C:25](=[O:28])[CH:26]=[CH2:27])([CH3:23])([CH3:22])[CH3:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:27]=[CH:26]/[C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:28])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 68453232HCID 68453232, compound

Product 1

HCID 131724410HCID 131724410, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 201B (5.00 g, 13.0 mmol), tert-butylacrylate (2.00 g, 15.6 mmol), palladium(II) acetate (175 mg, 0.78 mmol), and tri-o-tolylphosphine (951 mg, 3.12 mmol) in a sealed tube with triethylamine (8 mL) and acetonitrile (38 mL) was heated to 120° C. for 16 hours and then concentrated. The concentrate was purified by flash column chromatography on silica gel with 10-100% ethyl acetate/hexanes to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 10-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ab5a047fedc2456f9b1227c453520f5e
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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