Nitrogen → (E)-(2-Styryloxazol-4-yl)methanol

HRID 82815

反応式

HRID 82815 の反応式
N#N.[CH:3](/[C:11]1[O:12][CH:13]=[C:14]([C:16](OCC)=[O:17])[N:15]=1)=[CH:4]\[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1.CC(=O)OCC>[CH:3](/[C:11]1[O:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=1)=[CH:4]\[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 947NitrogenHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 5708074ethyl 2-[(E)-2-phenylethenyl]-1,3-oxazole-4-carboxylate

生成物 1

HCID 13657827(E)-(2-Styryloxazol-4-yl)methanol

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (E)-ethyl 2-styryloxazole-4-carboxylate (WO 2009077990 A1) (8.5 g, 34.9 mmol) in THF (28.3 mL) was treated dropwise at 0° C. with DiBAL-H (85.0 mL of a 1.0 M solution in toluene, 85.0 mmol) and the resulting solution was stirred for 1.5 h at 0° C. Rochelle's salt solution was added followed by EA and the mixture was stirred for 24 h at rt. The aq. layer was extracted with EA (3×40 mL) and the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound as an orange oil. TLC: rf (1:1 hept-EA)=0.20. LC-MS-conditions 07: tR=0.71 min, [M+H]+=202.15.

後処理

  1. stirringthe mixture was stirred for 24 h at rt
  2. extractionThe aq. layer was extracted with EA (3×40 mL)
  3. dry with materiallayers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-d289919e7d224af9845e4292dcbe03d5
出典データセット
uspto-grants-2014_09
特許番号
US08846733B2

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