Tetrahydrofuran → HCID 15508715, compound

HRID 1857302Notes

Reaction equation

HRID 1857302 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. ##STR8##

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-4af3bd2286a544aabea49689c8f8cb77
Source dataset
uspto-grants-2000_11
Patent number
US06146810

Reaction notes

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