Tributylamine → HCID 86757135, compound

HRID 1384178Notes

Reaction equation

HRID 1384178 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]([C:11]2[C:20]([CH3:21])=[CH:19][C:18]3[C:17]([CH3:23])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:25])([CH3:24])[C:13]=3[CH:12]=2)=[N:9][OH:10])[CH:5]=[CH:6][CH:7]=1.C(N(CCCC)CCCC)CCC.[C:39]([O:43][CH2:44][CH3:45])(=[O:42])[CH:40]=[CH2:41]>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[OH:10][NH:9][CH:8]([C:11]1[C:20]([CH3:21])=[CH:19][C:18]2[C:17]([CH3:23])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:25])([CH3:24])[C:13]=2[CH:12]=1)[C:4]1[CH:3]=[C:2]([CH:41]=[CH:40][C:39]([O:43][CH2:44][CH3:45])=[O:42])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7622TributylamineHCID 8821Ethyl AcrylateHCID 73752954HCID 73752954, compound

Product 1

HCID 86757135HCID 86757135, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of (3-iodophenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)methanone oxime (320 mg, 0.7 mmol), palladium diacetate (20 mg, 89 μmol), tributylamine (392 μl, 1.7 mmol) and ethyl acrylate (78 μl, 0.7 mmol) in acetonitrile (10 ml) is heated for 4 h at 80° C. The reaction medium is extracted with ethyl ether and washed with water. After drying, the organic phase is concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash- chromatography on a column of silica.

Workup

  1. extractionThe reaction medium is extracted with ethyl ether
  2. washwashed with water
  3. customAfter drying
  4. concentrationthe organic phase is concentrated on a rotary evaporator under vacuum at 40° C
  5. customThe product is purified by flash- chromatography on a column of silica

Sources & evidence

ORD record
ord-4698c7f3d2a44810839c45f61539c00d
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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