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Dimethyl Sulfoxide → methyl 4-[(2R)-2-formyl-3,4-dihydro-2H-chromen-6-yl]benzoate

HRID 896860
Notes
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Reaction equation

HRID 896860 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=3)[CH:19]=2)[O:14]1.C(N(CC)CC)C>C(Cl)Cl>[CH:12]([C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=3)[CH:19]=2)[O:14]1)=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 9900874methyl 4-[(2R)-2-(hydroxymethyl)-3,4-dihydro-2H-chromen-6-yl]benzoate

Product 1

HCID 9965972methyl 4-[(2R)-2-formyl-3,4-dihydro-2H-chromen-6-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of 33 mg (0.425 mmol) dimethyl sulfoxide in 2 mL of methylene chloride at −78° C., was added 0.14 mL (0.272 mmol) 2M oxalyl chloride. After the solution had stirred at this temperature for 10 minutes, a solution of 50 mg (0.17 mmol) methyl 4-[(2R)-2-(hydroxymethyl)-3,4-dihydro-2H-chromen-6-yl]benzoate (Example 16) in 2 mL of methylene chloride was added dropwise and the resulting mixture was stirred at −78° C. for an additional 1.6 hours. At this time, 0.14 mL (1.02 mmol) triethylamine was added to the mixture slowly, and then it was allowed to warm to room temperature over 15 minutes. The solution of desired product was used without further purification.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for an additional 1.6 hours
  2. customThe solution of desired product was used without further purification

Sources & evidence

ORD record
ord-e438f69c2a66408ca9c99194d4f94e58
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919371B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes