Propargyl alcohol → HCID 54086541, compound

HRID 1734405Notes

Reaction equation

HRID 1734405 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([C:6]([O:8][CH2:9][O:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:22]([OH:25])[C:23]#[CH:24]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:25][CH2:22][C:23]#[C:24][C:2]1[CH:21]=[CH:20][C:5]([C:6]([O:8][CH2:9][O:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([C:4]#[C:5][CH2:6][OH:7])=[CH:14][CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 131719455HCID 131719455, compound

Product 1

HCID 54086541HCID 54086541, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Bis (triphenylphosphine)palladium dichloride (17.0 mg, 0.02 mmol) and cuprous iodide (2.0 mg, 0.01 mmol) are added to a suspension of methylene bis (p-bromobenzoate) prepared as described in Example 4 (n) (0.500 g, 1.21 mmol) and propargyl alcohol (0.16 ml, 2.66 mmol) in triethylamine (10 ml) with good stirring, at 20° C., under a dry N2 atmosphere. After 10 days at 20° C., the triethylamine is removed under reduced pressure, water (20 ml) is added and the mixture is extracted with dichloromethane (3×15 ml). The dichloromethane phases are washed with hydrochloric acid (0.5M, 10 ml), dried (MgSO4) and the dichloromethane removed under reduced pressure to give 0.37 g (85%) of the crude product. 1H NMR (60 MHz, CDCl3): δ 3.67 (2 H, s, OH), 4.47 (4 H, s, CH2 --O), 6.18 (2 H, s, O--CH2 --O), 7.2-7.5 (4 H, Ar), 7.8-8.0 (4 H, Ar).

Workup

  1. customprepared
  2. customthe triethylamine is removed under reduced pressure, water (20 ml)
  3. additionis added
  4. extractionthe mixture is extracted with dichloromethane (3×15 ml)
  5. washThe dichloromethane phases are washed with hydrochloric acid (0.5M, 10 ml)
  6. dry with materialdried (MgSO4)
  7. customthe dichloromethane removed under reduced pressure

Sources & evidence

ORD record
ord-ffc533d7c3ef4d1f8649e8931a3f1074
Source dataset
uspto-grants-1996_07
Patent number
US05534250

Reaction notes

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