Diethyl Ether → HCID 67126522, compound

HRID 574772Notes

Reaction equation

HRID 574772 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4](OS(C(F)(F)F)(=O)=O)[CH2:3]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].CCOCC>C1(C)C=CC=CC=1.C(O)C.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>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:4]2[CH2:3][C:2]([CH3:20])([CH3:1])[O:7][CH2:6][C:5]=2[C:8]([O:10][CH3:11])=[O:9])=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 87279388HCID 87279388, compound

Product 1

HCID 67126522HCID 67126522, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of EXAMPLE 15B (2.88 g), 4-chlorophenylboronic acid (1.88 g) and Pd(Ph3P)4 (0.578 g) in toluene (40 mL) and ethanol (10 mL) was added 2N Na2CO3 (10 mL). The mixture was stirred at reflux overnight. The mixture was diluted ether (300 mL) and washed with water, brine and dried over Na2SO4. After evaporation of solvent, the residue was loaded on a column and eluted with 3% ethyl acetate in hexane to give the product.

Workup

  1. temperatureat reflux overnight
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of solvent
  5. washeluted with 3% ethyl acetate in hexane
  6. customto give the product

Sources & evidence

ORD record
ord-4d1af1aa27a84a75a4292457f88ac929
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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