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Hydrochloric Acid → Methyl 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate

HRID 1584345
ノート
印刷プレビュー

反応式

HRID 1584345 の反応式
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:10]([F:28])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].N12CCCN=C1CCCCC2.Cl>C1(C)C=CC=CC=1>[F:28][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:19][C:20]=1[CH3:21])[CH:7]=[CH:2][C:3]([O:5][CH3:6])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10983188Methyl 2-bromo-3-[3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionate

生成物 1

HCID 54362890Methyl 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate収率 86.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of methyl 2-bromo-3-[3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionate (14.1 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (4.8 g) and toluene (150 ml) was stirred for 2 hours at temperatures ranging from 80 to 90° C. The reaction mixture was poured into 2N HCl, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent under reduced pressure to yield methyl 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate (10.0 g). The product was recrystallized from dichloromethane-methanol to give colorless prisms, m.p.167-168° C.

後処理

  1. customranging from 80 to 90° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationby distilling off the solvent under reduced pressure

出典と根拠

ORDレコード
ord-a099c05d68434ed7acf0a24e2d4b7121
出典データセット
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05932601

反応ノート

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