Ammonium Chloride → 5-Cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

HRID 1516704Notes

Reaction equation

HRID 1516704 reaction equation
FC(F)(F)S(O[C:7]1[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=[C:13]2[C:8]=1[C:9](=[O:24])[CH2:10][C:11]([CH3:23])([CH3:22])[O:12]2)(=O)=O.[C:27]1(B(O)O)[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.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>[C:27]1([C:7]2[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=[C:13]3[C:8]=2[C:9](=[O:24])[CH2:10][C:11]([CH3:22])([CH3:23])[O:12]3)[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 38629021-Cyclohexenylboronic acidHCID 580029926-Formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 580029485-Cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 365 mg (930 μmol) of 6-formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (Example 19A), 152 mg (1.20 mmol) of cyclohex-1-en-1-ylboronic acid, 75 mg (60 μmol) of tetrakis(triphenylphosphine)palladium and 334 mg (1.57 mmol) of potassium phosphate in 5.5 ml of degassed dioxane is stirred at 100° C. overnight. After cooling to room temperature, ammonium chloride solution is added and the mixture is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate, the solvent is then removed under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase:cyclohexane/ethyl acetate 20:1).

Workup

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customthe solvent is then removed under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel (mobile phase:cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-7134e116541c44c5b336197b8cbb6ebe
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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