Triphenylphosphine → HCID 70495691, compound

HRID 523337

Reaction equation

HRID 523337 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[Br:14][CH:15](O)[CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:14][CH2:15][CH2:16][CH2:17][O:12][C:9]1[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:13])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 92203Methyl p-coumarateHCID 5363146Diisopropyl azodicarboxylateHCID 12887879Bromopropanol

Product 1

HCID 70495691HCID 70495691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 5 g (28.1 mmol) of 4-Hydroxycinnamic acid methyl ester, 4.9 g (35.1 mmol) of 4 bromopropanol, 9.2 g (35.1 mmol) of triphenylphosphine in 100 mL of THF are added 7.1 g (35.1 mmol) of diisopropylazodicarboxylate under inert atmosphere. The solution is heated up to reflux and allowed to stir overnight. After 20 hours, the reaction mixture is partitioned between EtOAc and water. The organic phase is washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation to give 7.5 g of (methyl (2E)-3-[4-(3-bromopropoxy)phenyl]prop-2-enoate.

Workup

  1. temperatureThe solution is heated up
  2. temperatureto reflux
  3. waitAfter 20 hours
  4. customthe reaction mixture is partitioned between EtOAc and water
  5. washThe organic phase is washed repeatedly with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-db9adabeb650425a934951281dbbebef
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Linked notes

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