1,3-Oxazole-2-carboxaldehyde → HCID 59855140、化合物

HRID 731171

反応式

HRID 731171 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.[O:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]=[O:22]>C1COCC1>[O:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:9][CH:10]=1)[OH:22]

参加物

4

反応物 2

HCID 147866091,3-Oxazole-2-carboxaldehydeHCID 178419637HCID 178419637、化合物

生成物 1

HCID 59855140HCID 59855140、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4-(2-Tetrahydro-3-H-pyranoxy)phenylmagnesium bromide (6.7 mmol) in THF (0.5 M) was added dropwise to a solution of oxazole-2-carbaldehyde (5.15 mmol) in THF (8 mL). After it was stirred at room temperature for 2.5 hours, the reaction was quenched with water and extracted with EtOAc (200 mL). The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was column chromatographed (silica gel, 1:2 EtOAc/hexane). Compound M11.1 was obtained. MS ESI (pos.) m/e:276 (M+H). 1H NMR (400 MHz) (DMSO-d6) δ 8.02 (s, 1H); 7.31 (d, J=8.7 Hz, 2H); 7.14 (s, 1H); 6.97-7.01 (m, 2H); 6.27 (d, J=5 Hz, 1H); 5.74 (d, J=5 Hz, 1H); 5.44 (s, 1H); 3.74 (m, 1H); 3.52 (M, 1H); 1.72-1.81 (m, 3H); 1.52-1.60(m, 4H).

後処理

  1. customthe reaction was quenched with water
  2. extractionextracted with EtOAc (200 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed (silica gel, 1:2 EtOAc/hexane)
  8. customCompound M11.1 was obtained

出典と根拠

ORDレコード
ord-acb326583f6a446885ad4ae9dba9e2bd
出典データセット
uspto-grants-2009_09
特許番号
US07582803B2

関連ノート

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