1,4-Dioxane → HCID 66764657, compound

HRID 402798Notes

Reaction equation

HRID 402798 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[O:10][CH2:9][CH:8]=1)(=O)=O.[CH:23]1(B2OC(C)(C)C(C)(C)O2)[CH2:25][CH2:24]1.O.[OH-].[Li+].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].O>[CH:23]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=3)[O:10][CH2:9][CH:8]=2)[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 88911424HCID 88911424, compound

Product 1

HCID 66764657HCID 66764657, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 4-{[(trifluoromethyl)sulfonyl]oxy}-2H-chromene-6-carboxylate (596 mg, 1.76 mmol), cyclopropylboronic acid pinacol ester (803 μL, 4.40 mmol), lithium hydroxide monohydrate (185 mg, 4.40 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (387 mg, 0.53 mmol) were mixed in a microwave vial and dioxane (4.40 mL) and water (1.50 mL) were added. The reaction mixture was heated to 120° C. for 30 minutes under microwave irradiation before concentrating under vacuum. The crude residue was purified by silica gel chromatography to afford the desired product as a pale-yellow oil.

Workup

  1. additionwere added
  2. concentrationbefore concentrating under vacuum
  3. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6e7ed53766a2420aa43a0397b337d656
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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