Dichloromethane → Methyl 4-[4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]benzoate

HRID 2355997Notes

Reaction equation

HRID 2355997 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:9][CH:8]=1)(=O)=O.[CH3:19][O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].C(Cl)Cl.[F-].[Cs+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:13]([CH:10]1[CH2:11][CH2:12][C:7]([C:26]2[CH:27]=[CH:28][C:23]([C:21]([O:20][CH3:19])=[O:22])=[CH:24][CH:25]=2)=[CH:8][CH2:9]1)([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 27343694-Methoxycarbonylphenylboronic acidHCID 10935034HCID 10935034, compound

Product 1

HCID 22730509Methyl 4-[4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]benzoate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 5A (286 mg, 1.0 mmol), (4-methoxycarbonylphenyl)-boronic acid (216 mg, 1.2 mmol), Pd(dppf)Cl2.CH2Cl2 (37 mg, 0.05 mmol), and cesium fluoride (454 mg, 3.0 mmol) in dioxane (5 mL) was heated to 90° C., stirred for 16 hours, filtered through a pad of silica gel (10 g) with diethyl ether (5 mL) and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes to provide the desired product.

Workup

  1. filtrationfiltered through a pad of silica gel (10 g) with diethyl ether (5 mL)
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e907d802de8a4a50a81608281c3fe82d
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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