CID 406 → HCID 54032013, 화합물

HRID 967737노트

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HRID 967737 반응식
[H-].[Na+].P(=O)([O-])O[C:5]([CH2:14][CH3:15])(CC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.P(=O)([O-])[O-].[CH3:22][C:23]1[N:24]=C(C=O)[S:26][CH:27]=1>COCCOC.C(OCC)(=O)C>[CH3:22][C:23]1[N:24]=[C:15]([CH:14]=[CH:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:26][CH:27]=1

참가 물질

7

반응물 4

HCID 406CID 406HCID 24758Sodium hydride2회HCID 42634324-Methyl-1,3-thiazole-2-carbaldehydeHCID 178447633HCID 178447633, 화합물

생성물 1

HCID 54032013HCID 54032013, 화합물수율 16%

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Sodium hydride (102 mg of a 60% suspension in mineral oil, 4.3 mmol) was slurried in dry 1,2-dimethoxyethane (DME) under argon, cooled to 0° C. in an ice bath, and diethylbenzyl phosphonate (0.89 mL, 4.3 mmol) was added dropwise to the suspension. Thirty minutes after the completion of the phosphonate addition, 4-methylthiazole-2-carboxaldehyde (120 mg, 0.94 mmol) was added as a solution in DME (5 mL). After stirring for 4 h, further NaH (40 mg of a 60% suspension in mineral oil, 1.0 mmol) was added and the reaction mixture was allowed to warm to ambient temperature and stir for 16 h. The reaction mixture was quenched by the addition of water (20 mL) and ethyl acetate (50 mL). The aqueous phase was extracted with ethyl acetate (2×30 mL), the combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with 90:10 hexane:ethyl acetate to afford 4-methyl-2-[2-phenylethenyl]-1,3-thiazole (30 mg, 16% yield) as an oil. 1H NMR analysis showed the material to be a 10:1 mixture of E and Z isomers (spectral data are reported for the major isomer). 1H NMR (CDCl3,300 MHz) δ: 7.54-7.51 (m, 2H) 7.42-7.23 (m, 5H) 6.80 (s, 1H) 2.47 (s, 3H). MS (ESI) (minor isomer) 202.2 (M++H), (major isomer) 201.6 (M+).

후처리

  1. temperatureto warm to ambient temperature
  2. stirringstir for 16 h
  3. customThe reaction mixture was quenched by the addition of water (20 mL) and ethyl acetate (50 mL)
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×30 mL)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography on silica gel eluting with 90:10 hexane

출처 및 근거

ORD 기록
ord-1bf5a34f982441ba9b8bbfa4d7d2df56
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956049B1

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