Acetone → HCID 12135314, compound

HRID 2100251Notes

Reaction equation

HRID 2100251 reaction equation
Br/[C:2](/[F:16])=[C:3](/[F:15])\[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26].C([O-])([O-])=O.[Na+].[Na+].CC(C)=O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:16]/[C:2](/[C:21]1[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=1)=[C:3](\[F:15])/[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 12135313HCID 12135313, compound

Product 1

HCID 12135314HCID 12135314, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 90 mg (0.31 mmol; 1 eq.) of (9), 198 mg (0.93 mmol; 3 eq.) of 3,4,5-trimethoxyphenyl-boronic acid, 0.6 mL of Na2CO3 2M aqueous solution and 19 mg (0.0016 mmol; 0.05 eq.) of Pd(Ph3P)4 in 4 mL toluene was refluxed for 2.5 h. The solution was then cooled down to room temperature, dried over anhydrous sodium sulfate and the crude mixture was passed through a short silica gel column to remove catalyst. The crude product was purified by chromatography on silica gel with Hexane/Acetone 8:2 to give 57 mg (0.15 mmol; 48%) of a yellow oil. Rf=0.17 in Hex./Acetone 8:2.

Workup

  1. temperaturewas refluxed for 2.5 h
  2. dry with materialdried over anhydrous sodium sulfate
  3. customto remove catalyst
  4. customThe crude product was purified by chromatography on silica gel with Hexane/Acetone 8:2
  5. customto give 57 mg (0.15 mmol; 48%) of a yellow oil

Sources & evidence

ORD record
ord-3a1a70df229e470bba75de5bac095307
Source dataset
uspto-grants-2009_08
Patent number
US07572778B2

Reaction notes

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