Potassium Carbonate → 8-(4-Chlorophenyl)spiro[4.5]dec-8-ene-9-carbaldehyde

HRID 2040155Notes

Reaction equation

HRID 2040155 reaction equation
Cl[C:2]1[CH2:11][CH2:10][C:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]=1[CH:12]=[O:13].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH2:11][CH2:10][C:5]3([CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:4][C:3]=2[CH:12]=[O:13])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 16028TetrabutylammoniumHCID 742994-Chlorophenylboronic acidHCID 866481768-Chlorospiro[4.5]dec-7-ene-7-carbaldehyde

Product 1

HCID 872950068-(4-Chlorophenyl)spiro[4.5]dec-8-ene-9-carbaldehyde

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of EXAMPLE 71A (3 g) in water (50 mL) was added 4-chlorophenylboronic acid (2.83 g), tetrabutylammonium (4.87 g), potassium carbonate (6.26 g) and palladium(II) acetate (0.169 g). The reaction mixture was stirred at 45° C. for 5 hours and extracted with dichloromethane. The organic layer was concentrated and the residue was loaded onto a silica gel column, and eluted with 5-20% ethyl acetate in hexane to give the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic layer was concentrated
  3. washeluted with 5-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b68128ca9e404dcb82f21801aa9ab04d
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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