Oxalyl chloride → 7-chlorocarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl adamantanecarboxylate

HRID 926440Notes

Reaction equation

HRID 926440 reaction equation
[C:1]12([C:11]([O:13][CH:14]3[CH:18]4[O:19][C:20](=[O:26])[CH:21]5[CH:22]([C:23](O)=[O:24])[CH:15]3[CH2:16][CH:17]45)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(Cl)(=O)C([Cl:30])=O>C1(C)C=CC=CC=1>[C:1]12([C:11]([O:13][CH:14]3[CH:18]4[O:19][C:20](=[O:26])[CH:21]5[CH:22]([C:23]([Cl:30])=[O:24])[CH:15]3[CH2:16][CH:17]45)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 1181291646-adamantanecarbonyloxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-7-carboxylic acid

Product 1

HCID 1181291597-chlorocarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl adamantanecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 420 ml of toluene was suspended 60 g of the carboxylic acid (23) obtained in Synthesis Example 1-1-2. At 80° C., 25.3 g of oxalyl dichloride was added dropwise to the suspension, which was stirred for 4 hours. The toluene was distilled off in vacuum, obtaining the target compound. The resulting acid chloride was used in the subsequent reaction without further purification.

Workup

  1. customobtained in Synthesis Example 1-1-2
  2. distillationThe toluene was distilled off in vacuum
  3. customobtaining the target compound

Sources & evidence

ORD record
ord-85b39fa95c7a4c359bd7c0acf163ab2a
Source dataset
uspto-grants-2016_03
Patent number
US09285678B2

Reaction notes

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