Diethyl Ether → methyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-oxoacetate

HRID 591066노트

반응식

HRID 591066 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([C:18](=[O:22])[C:19]([OH:21])=[O:20])=[C:13]([CH3:17])[S:14][C:15]=3[CH3:16])=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.[CH3:23][Si](C=[N+]=[N-])(C)C.C(OCC)C>CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([C:18](=[O:22])[C:19]([O:21][CH3:23])=[O:20])=[C:13]([CH3:17])[S:14][C:15]=3[CH3:16])=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 708551932-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-2-oxoacetic acid

생성물 1

HCID 70818547methyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-oxoacetate수율 72%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]-2-oxoacetic acid (42a) (1.09 g, 3.43 mmol) in methanol (10 mL) was cooled to 0° C. Trimethylsilyldiazomethane 2N in diethyl ether (6.89 mL, 13.7 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 3 hours. The precipitate was filtered off and washed with cooled methanol (5 mL). The filtrate was concentrated in vacuo and the residue was dissolved in a minimum of methanol. The solution was sonicated for a few seconds and the precipitate was filtered and washed with cooled methanol. The precipitates were combined to provide the desired ester (42b) (820 mg, 2.48 mmol, 72% over two steps) as a beige solid, which was used without further purification.

후처리

  1. filtrationThe precipitate was filtered off
  2. washwashed with cooled methanol (5 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in a minimum of methanol
  5. customThe solution was sonicated for a few seconds
  6. filtrationthe precipitate was filtered
  7. washwashed with cooled methanol

출처 및 근거

ORD 기록
ord-7ab3cd17c5244754a75c95d61edf080b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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