Dimethylformamide → HCID 69489339, compound

HRID 851972Notes

Reaction equation

HRID 851972 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[CH2:2][CH:3]=[CH2:4].C(=O)([O-])[O-].[K+].[K+].Br[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18].CN(C)C=O>C1COCC1>[CH3:7][O:6][C:1](=[O:5])[CH2:2][CH2:3][CH2:4][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 728502-Bromobenzyl alcoholHCID 77314Methyl 3-butenoate

Product 1

HCID 69489339HCID 69489339, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To an ice cooled solution of methyl 3-butenoate (2.0 g, 20 mmol) in THF (20 ml) 9-borabicyclo(3,3,1)nonane (49 ml, 0.5M in tetrahydrofurane) was added within 1 hour. After additional stirring for 4.5 hours potassium carbonate (7.5 g, 54 mmol), 2-bromobenzyl alcohol (3.4 g, 18.2 mmol), dimethylformamide (60 ml) and palladium (dppf)-dichloride (0.665 g, 0.91 mmol) were added and the mixture was stirred at 60° C. overnight. After cooling the mixture was filtered over Celite and evaporated. The residue was purified by column chromatography (eluent hexane/ethyl acetate: 4:1 gradually to 1:1) to yield 2.46 g (65%) of product.

Workup

  1. additionwere added
  2. temperatureAfter cooling the mixture
  3. filtrationwas filtered over Celite
  4. customevaporated
  5. customThe residue was purified by column chromatography (eluent hexane/ethyl acetate

Sources & evidence

ORD record
ord-d4552d3fa07d47a3bf4c6b900ccc4ff0
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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