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Diethyl Ether → HCID 86680491, 화합물

HRID 1497471
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HRID 1497471 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH:13]=[O:14])=[N:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:15]([Mg]Br)[CH3:16].C(OCC)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH:13]([OH:14])[CH2:15][CH3:16])=[N:10][N:9]=2)=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 218062345-Formyl-2-(4-fluorophenyl)-1,3,4-thiadiazoleHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 86680491HCID 86680491, 화합물수율 45%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-(4-fluorophenyl)-1,3,4-thiadiazole-2-carbaldehyde (0.2 g, 0.96 mmol) in THF (8 mL) was added 3.0 M solution of ethyl magnesium bromide in diethyl ether (0.96 mL, 2.9 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 2 h. The reaction mixture was quenched with saturated ammonium chloride solution (15 mL) and water (15 mL), and extracted with ethyl acetate (100 mL). The organic extracts were dried over sodium sulphate and concentrated under reduced pressure to afford 1-(5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)propan-1-ol as a yellow solid (0.10 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.0-8.03 (m, 1H), 7.39-7.35 (m, 2H), 6.36 (d, 1H), 4.92-4.89 (m, 1H), 1.89-1.78 (m, 2H), 0.95 (t, 3H); LC-MS m/z calcd for [M+H]+ 239.06. found 239.1.

후처리

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution (15 mL) and water (15 mL)
  2. extractionextracted with ethyl acetate (100 mL)
  3. dry with materialThe organic extracts were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aeb1b27a63754118966f32a2e7997b4d
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199975B2

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