Tributylamine → HCID 21185896, compound

HRID 1384167Notes

Reaction equation

HRID 1384167 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=C[C:3]=1[C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]2([CH3:23])[CH3:22])=[CH2:9].C(N(CCCC)CCCC)CCC.[C]=O.[C:39]([O:42][CH2:43]C)(=[O:41])[CH3:40]>CO.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:20][C:16]1([CH3:21])[CH2:15][CH2:14][C:13]([CH3:22])([CH3:23])[C:12]2[CH:11]=[C:10]([C:8]([C:3]3[CH:2]=[CH:7][CH:6]=[CH:5][C:40]=3[C:39]([O:42][CH3:43])=[O:41])=[CH2:9])[CH:19]=[CH:18][C:17]1=2

Participants

7

Reactant 4

HCID 7622TributylamineHCID 8857Ethyl AcetateHCID 21185925HCID 21185925, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 21185896HCID 21185896, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-[1-(2-iodophenyl)vinyl]-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (9.5 g, 22 mmol), palladium diacetate (560 mg, 2.5 mmol)-and tributylamine (12 ml, 50 mmol) in methanol (500 ml) is heated for 3 h at 100° C. under a pressure of carbon monoxide (3 bar). After concentration on an evaporator under vacuum at 40° C., the oil obtained is diluted in ethyl acetate and washed three times with water. The product is purified by flash chromatography on a column of silica.

Workup

  1. concentrationAfter concentration
  2. customon an evaporator under vacuum at 40° C.
  3. customthe oil obtained
  4. washwashed three times with water
  5. customThe product is purified by flash chromatography on a column of silica

Sources & evidence

ORD record
ord-a30675f8048049f5aac1350593660369
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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