Tetrahydrofuran → HCID 15508715, compound

HRID 840953Notes

Reaction equation

HRID 840953 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[O:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>>[C:6]([O:5][C:3](=[O:4])[CH2:2][CH:14]([CH:13]1[CH2:8][CH:6]2[CH2:9][CH:12]1[CH:11]=[CH:7]2)[OH:10])([CH3:9])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 79177tert-Butyl bromoacetate

Product 1

HCID 15508715HCID 15508715, compound

Conditions

Temperature
70 °C

Procedure

In a four-necked flask equipped with a stirrer and a reflux condenser were placed 50 g of a Zn—Cu couple and 90 ml of tetrahydrofuran, followed by slowly charging a solution of 53 ml of t-butyl bromoacetate and 36 ml of 5-norbornen-2-carboxyaldehyde in 180 ml of tetrahydrofuran. After completion of the charging, the solution was subjected to reflux at 70° C. for 2 hours and then, cooled to room temperature. The Zn—Cu couple was filtered off, after which the solution was washed and extracted with the same solvent and distilled under vacuum to give 39 g of 3-bicyclo[2,2,1]hept-5-en-2-yl-3-hydroxy-propionic acid t-butyl ester (BHP) monomer, represented by the following structural formula M-I.

Workup

  1. customIn a four-necked flask equipped with a stirrer and a reflux condenser
  2. temperaturecooled to room temperature
  3. filtrationThe Zn—Cu couple was filtered off
  4. washafter which the solution was washed
  5. extractionextracted with the same solvent
  6. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-5396cf7f66e54772bff4f08350e878e6
Source dataset
uspto-grants-2002_04
Patent number
US06369143B1

Reaction notes

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