Tributylamine → HCID 21185946, compound

HRID 1384162Notes

Reaction equation

HRID 1384162 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][C:19]=1[CH3:20])[C:16]([CH3:22])([CH3:21])[CH2:15][CH2:14][C:13]2([CH3:24])[CH3:23])=[CH2:9].C(N(CCCC)CCCC)CCC.[C]=O.[C:40]([O:43][CH2:44]C)(=[O:42])[CH3:41]>CO.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:20][C:19]1[C:10]([C:8]([C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][C:41]=2[C:40]([O:43][CH3:44])=[O:42])=[CH2:9])=[CH:11][C:12]2[C:13]([CH3:24])([CH3:23])[CH2:14][CH2:15][C:16]([CH3:21])([CH3:22])[C:17]=2[CH:18]=1

Participants

7

Reactant 4

HCID 7622TributylamineHCID 8857Ethyl AcetateHCID 21185948HCID 21185948, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 21185946HCID 21185946, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-[1-(2-iodophenyl)vinyl]-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (17.2 g, 40 mmol), palladium diacetate (1.02 g, 4.5 mmol) and tributylamine (21.9 ml, 92 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-9b06dcb909a141cf93ba0f47895d11bd
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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