Tetrahydrofuran → HCID 15508715, compound

HRID 277653Notes

Reaction equation

HRID 277653 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[O:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>>[C:1]([O:5][C:6](=[O:9])[CH2:7][CH:14]([CH:13]1[CH2:3][CH:1]2[CH2:4][CH:12]1[CH:11]=[CH:2]2)[OH:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 79177tert-Butyl bromoacetate

Product 1

HCID 15508715HCID 15508715, compound

Conditions

Temperature
70 °C

Procedure

A couple of Zn—Cu (50 g) and tetrahydrofuran (90 ml) were placed in a four-necked round flask equipped with a stirrer and reflux condenser and then, a mixing solution of t-butylbromoacetate (53 ml) and 5-norbornene-2-carboxaadehyde (36 ml) dissolved in tetrahydrofuran 180 ml was slowly added to the flask. The resulting solution was refluxed at 70° C. for 2 hours and cooled into room temperature. After separating a couple of Zn—Cu from the solution, the remaining solution was extracted, washed with a solvent and distilled under reduced pressure to obtain 3-bicyclo[2,2,1]hept-5-ene-2-yl-3-hydroxyl-propionic acid t-butyl ester (hereinafter referred to as “BHP”, M-I) as a monomer (39 g).

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser
  3. additionwas slowly added to the flask
  4. temperaturecooled into room temperature
  5. customAfter separating a couple of Zn—Cu from the solution
  6. extractionthe remaining solution was extracted
  7. washwashed with a solvent
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-69f4ab8d651749e08cb945db6393eb9f
Source dataset
uspto-grants-2002_03
Patent number
US06358666B1

Reaction notes

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