Oxalyl chloride → HCID 18780160, compound

HRID 376584Notes

Reaction equation

HRID 376584 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][CH:7]([C:9]([OH:11])=O)[CH2:6][CH2:5]1.C(Cl)(=O)[C:13]([Cl:15])=O>ClCCl.CN(C)C=O>[Cl:15][CH2:13][C:9]([CH:7]1[CH2:6][CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8]1)=[O:11]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 187800165-(Methoxymethyl)oxolane-2-carboxylic acid

Product 1

HCID 18780160HCID 18780160, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (2RS,5SR)-5-methoxymethyltetrahydrofuran-2-carboxylic acid (3.1g) in dichloromethane (50ml) was treated with oxalyl chloride (2.68ml) and dimethylformamide (1 drop). The mixture was stirred for 1h and heated to reflux for 10 mins. The solvent was evaporated and then dichloromethane was evaporated from the residue twice. The product was dissolved in dichloromethane (100ml) and the solution cooled in an ice bath. Diazomethane was then passed into the solution as described in Example 14(a). When the addition was complete the mixture was stirred at 0° C. for 0.5h and then hydrogen chloride gas was passed into the solution until all the diazoketone had been consumed. The solution was washed with brine, dried over magnesium sulphate and evaporated. The title compound (2.44g) was isolated by column chromatography using gradient elution (silica gel, 4:1 going to 1:1 hexane : ethyl acetate); vmax (film) 1740cm-1 ; δH (CDCl3) 1.6-2.35 (4H,m), 3.30-3.75 (2H,m), 3.37 (3H,s) and 4.05-4.75 (4H,m).

Workup

  1. temperatureheated
  2. temperatureto reflux for 10 mins
  3. customThe solvent was evaporated
  4. customdichloromethane was evaporated from the residue twice
  5. dissolutionThe product was dissolved in dichloromethane (100ml)
  6. temperaturethe solution cooled in an ice bath
  7. additionWhen the addition
  8. customhad been consumed
  9. washThe solution was washed with brine
  10. dry with materialdried over magnesium sulphate
  11. customevaporated

Sources & evidence

ORD record
ord-778eefff638942efae0b48d9bdb267c8
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

Loading…