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

HRID 47674Notes

Reaction equation

HRID 47674 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]

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 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethyl sulfoxide (33 mg, 0.425 mmol) in methylene chloride (2 mL) at −78° C., was added 0.14 mL of 2 M oxalyl chloride (0.272 mmol). After the solution had stirred at this temperature for 10 minutes, a solution of methyl 4-[(2R)-2-(hydroxymethyl)-3,4-dihydro-2H-chromen-6-yl]benzoate (50 mg, 0.17 mmol) in methylene chloride (2 mL) was added dropwise and the resulting mixture was stirred at −78° C. for an additional 1.6 hours. At this time, triethylamine (0.14 mL, 1.02 mmol) 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 directly in following steps.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for an additional 1.6 hours

Sources & evidence

ORD record
ord-b5475f0ab04b44948ee6b195049fa0af
Source dataset
uspto-grants-2004_03
Patent number
US06699860B2

Reaction notes

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