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

HRID 896860
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HRID 896860 반응식
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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e438f69c2a66408ca9c99194d4f94e58
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06919371B2

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