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Methyl Acrylate → trans-3-[2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphth-6-yl]prop-2-enoic acid methyl ester

HRID 1669
Notes
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Reaction equation

HRID 1669 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:6][CH2:5]2.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:24][O:23][C:19](=[O:22])/[CH:20]=[CH:21]/[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:6][CH2:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 196920336-bromo-2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 86752211trans-3-[2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphth-6-yl]prop-2-enoic acid methyl esterYield 28.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.1 g (0.01 mol) of 6-bromo-2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphthalene are dissolved in 50 ml of dimethylformamide. There are added in succession to that solution 0.94 g (0.011 mol) of methyl acrylate, 22.4 mg (0.1 mmol) of palladium acetate, 121 mg (0.4 mmol) of tri-ortho-tolylphosphine and 1.6 ml (0.011 mol) of triethylamine. The mixture is heated at 125°-130° C. for 3 h 30 min. with stirring, cooled, poured into 700 ml of water, extracted with ethyl acetate and washed with a solution of LiCl. After acid to base change, 0.9 g of the expected product is obtained.

Workup

  1. temperatureThe mixture is heated at 125°-130° C. for 3 h 30 min.
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washwashed with a solution of LiCl

Sources & evidence

ORD record
ord-308160af0fe341559cc3cb76dcacfde8
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726208

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes