Tetrahydrofuran → 1-Benzyloxymethyl-3-hydroxyphenylmethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097518ノート

反応式

HRID 2097518 の反応式
[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[N:16][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:18](=[O:19])[C:13]=2[C:12](C=O)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1[CH2:34][CH2:33][CH2:32][CH2:31]1.[C:35]1([Mg]Br)[CH:40]=CC=C[CH:36]=1.[Cl-].[NH4+].[O:45]1CCCC1>>[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[N:16][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])[C:18](=[O:19])[C:13]=2[C:12]([OH:45])=[C:11]1[CH2:31][C:32]1[CH:40]=[CH:35][CH:36]=[CH:34][CH:33]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 866270441-Benzyloxymethyl-3-formyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 178420626HCID 178420626、化合物

生成物 1

HCID 666028001-Benzyloxymethyl-3-hydroxyphenylmethyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one収率 73%

実験手順

To 87 ml of dehydrated tetrahydrofuran solution containing 3.60 g (8.71 mmol) of 1-benzyloxymethyl-3-formyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one obtained in Reference example 33-(d) were added 12.2 ml of 1M phenyl magnesium bromide tetrahydrofuran solution under ice-cooling and under argon atmosphere, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, to the reaction mixture were added a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride, and the mixture was extracted with ethyl acetate. The organic layer after separation was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=4:1→1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 3.12 g of the title compound as a yellowish oil. (Yield: 73%)

後処理

  1. temperaturecooling and under argon atmosphere
  2. customAfter completion of the reaction
  3. extractiona saturated aqueous solution of sodium chloride, and the mixture was extracted with ethyl acetate
  4. customThe organic layer after separation
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionthe fractions containing the desired compound
  8. concentrationwere concentrated under reduced pressure

出典と根拠

ORDレコード
ord-c46d1b3eccd34bb7ad217bb732e3cf9b
出典データセット
uspto-grants-2013_05
特許番号
US08450319B2

反応ノート

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