Oxalyl chloride → 7-Chlorocarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furane-6-yl Methacrylate

HRID 75084Notes

Reaction equation

HRID 75084 reaction equation
[C:1]([O:6][CH:7]1[CH:11]2[O:12][C:13](=[O:19])[CH:14]3[CH:15]([C:16](O)=[O:17])[CH:8]1[CH2:9][CH:10]23)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(Cl)(=O)C([Cl:23])=O>C1(C)C=CC=CC=1>[C:1]([O:6][CH:7]1[CH:11]2[O:12][C:13](=[O:19])[CH:14]3[CH:15]([C:16]([Cl:23])=[O:17])[CH:8]1[CH2:9][CH:10]23)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 206800246-Methacryloyloxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furane-7-carboxylic Acid

Product 1

HCID 866409437-Chlorocarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furane-6-yl Methacrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Suspended into 135 mL of toluene was 18.0 g of the carboxylic acid (26) obtained in Synthesis Example 1-1-2, and then into the resulting suspension was gradually added 10.3 g of oxalyl chloride at 80° C. After this mixture was stirred for 4 hours, toluene was removed by distillation under reduced pressure to obtain the intended product. The obtained acid chloride was used in the next reaction without further purification.

Workup

  1. customobtained in Synthesis Example 1-1-2
  2. customat 80° C
  3. customtoluene was removed by distillation under reduced pressure
  4. customto obtain the intended product

Sources & evidence

ORD record
ord-fe22ae6ffcae43baacdaa4e45626e590
Source dataset
uspto-grants-2014_09
Patent number
US08835097B2

Reaction notes

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