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tert-Butyl acrylate → 4-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid Methyl Ester

HRID 220820
Notes
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Reaction equation

HRID 220820 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15].C([O-])(=O)C.[Na+]>CC(N(C)C)=O.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>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2](/[CH:15]=[CH:14]/[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:3]([CH3:12])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 15458tert-Butyl acrylateHCID 517045Sodium AcetateHCID 3294148Methyl 4-bromo-3-methylbenzoate

Product 1

HCID 575553844-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid Methyl EsterYield 40.2%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (5.0 g, 4.33 mmol) was added to a stirred solution of methyl 4-bromo-3-methylbenzoate (9.93 g, 43.3 mmol), tert-butyl acrylate (50 ml, 341.3 mmol) and sodium acetate (35.8 g, 436.4 mmol) in DMA (350 ml). The mixture was heated at 140° C. for 5 h, filtered through Celite® filter agent and the filtrate was concentrated in vacuo. The residue was redissolved in EtOAc, washed with 0.3M KHSO4 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane to 20% EtOAc:80% hexane) to yield the title compound (4.81 g, 40%).

Workup

  1. filtrationfiltered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was redissolved in EtOAc
  5. washwashed with 0.3M KHSO4
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane to 20% EtOAc:80% hexane)

Sources & evidence

ORD record
ord-1f0a08724f0c49a089dcf31bcc33b40b
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202858B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes