Hydrochloric Acid → methyl (4E)-4-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]-3-methoxyphenyl]methoxyimino]-4-phenylbutanoate

HRID 584531

反応式

HRID 584531 の反応式
Cl[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:22][CH3:23])[CH:4]=1.[OH:24]/[N:25]=[C:26](/[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)\[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].[H-].[Na+].Cl>CN(C)C=O.O>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:11]1[O:12][C:13]([CH3:14])=[C:9]([CH2:8][O:7][C:6]2[CH:20]=[CH:21][C:3]([CH2:2][O:24]/[N:25]=[C:26](/[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)\[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:4][C:5]=2[O:22][CH3:23])[N:10]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoateHCID 223445974-(4-Chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazole

生成物 1

HCID 22344612methyl (4E)-4-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]-3-methoxyphenyl]methoxyimino]-4-phenylbutanoate収率 64.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 4-(4-chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazole (1.65 g) and methyl E-4-hydroxyimino-4-phenylbutyrate (1.04 g) in N,N-dimethylformamide (20 ml) was added sodium hydride (60% in oil, 200 mg) at 0° C. After stirring for 1 hour, the reaction mixture was poured into water, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4), and concentrated. The residue was purified by column chromatography on silica gel. Elution with ethyl acetate-hexane (1:4, v/v) gave methyl E-4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxyimino]-4-phenylbutyrate (1.60 g, yield 64%) as crystals. Recrystallization from ethyl acetate-hexane gave pale yellow prisms. m.p. 67-69° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel
  6. washElution with ethyl acetate-hexane (1:4, v/v)

出典と根拠

ORDレコード
ord-ef3e46a40224462cbe7732a7dd6f014b
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

関連ノート

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