Pyridine → HCID 18992056, compound

HRID 375745Notes

Reaction equation

HRID 375745 reaction equation
[C:1]([O:20][CH2:21][CH2:22][C:23]([O-:25])=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].N1C=CC=CC=1.C(Cl)(=O)C([Cl:36])=O>C1(C)C=CC=CC=1>[C:1]([O:20][CH2:21][CH2:22][C:23]([Cl:36])=[O:25])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 23661807HCID 23661807, compound

Product 1

HCID 18992056HCID 18992056, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 3.30 g of potassium 3-trityloxypropionate in 75 ml of toluene, cooled to 0° C., was added 0.5 ml of pyridine, and subsequently 15 ml of oxalyl chloride were added within 10 minutes. The mixture was stirred for 30 minutes at room temperature and then evaporated in vacuo. The oily residue was taken up in 30 ml of toluene, and the solvent was evaporated in vacuo. The residue was taken up in 50 ml of methylene chloride and 50 ml of hexane, and the solution was stirred at 0° C. Unsoluble material was filtered off, and the filtrate was evaporated in vacuo to yield 2.81 g of 3-trityloxypropionyl chloride as a white solid.

Workup

  1. additionwere added within 10 minutes
  2. customevaporated in vacuo
  3. customthe solvent was evaporated in vacuo
  4. stirring50 ml of hexane, and the solution was stirred at 0° C
  5. filtrationUnsoluble material was filtered off
  6. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-4fa21c2a87b34964b1feefcca0d743f4
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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