Propargyl alcohol → HCID 21964572, compound

HRID 2212325Notes

Reaction equation

HRID 2212325 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].Br[C:6]1[CH:7]=[C:8]([CH:13]=[C:14](Br)[C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:9]([O:11][CH3:12])=[O:10]>C(N(CC)CC)C.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>[OH:4][CH2:1][C:2]#[C:3][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:3]#[C:2][CH2:1][OH:4])[C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 23245049HCID 23245049, compound

Product 1

HCID 21964572HCID 21964572, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Pd(Ph3P)4 (0.27 g), CuBrSMe2 (0.11 g) and propargyl alcohol (0.72 g, 12.9 mmol) are added successively to a solution of dimethyl 3,5-dibromoterephthalate (Al 15, 2.0 g, 5.7 mmol) in triethylamine (40 ml), and the mixture is stirred at RT for 10 min and then under reflux at 80° C. for 3.5 h. After cooling, the reaction mixture is filtered off with suction through kieselguhr and washed with ethyl acetate (20 ml). The organic phase is concentrated under reduced pressure. Further purification is carried out by chromatography [toluene/acetone (8:2)] on a silica gel column. This gives the title compound (1.4 g) as a colorless solid. TLC, silica gel (glass plates), [toluene/acetone (8:2)], Rf=0.20.

Workup

  1. temperatureunder reflux at 80° C. for 3.5 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered off with suction through kieselguhr
  4. washwashed with ethyl acetate (20 ml)
  5. concentrationThe organic phase is concentrated under reduced pressure
  6. customFurther purification

Sources & evidence

ORD record
ord-dcc9870740a2423197fdfc5053e7c62b
Source dataset
uspto-grants-2006_09
Patent number
US07101911B2

Reaction notes

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