Ammonium Chloride → {1-Cyano-3-ethyl-5-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-pent-3-enyl}-phosphonic Acid Diethyl Ester

HRID 33657

反応式

HRID 33657 の反応式
[C:1]([CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:23][C:24]([CH2:47][CH3:48])=[CH:25][CH2:26][C:27]1[C:35]([O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])=[C:34]2[C:30]([CH2:31][O:32][C:33]2=[O:43])=[C:29]([CH3:44])[C:28]=1[O:45][CH3:46].[Cl-].[NH4+]>C1COCC1>[CH2:6]([O:5][P:4]([CH:3]([C:1]#[N:2])[CH2:23][C:24]([CH2:47][CH3:48])=[CH:25][CH2:26][C:27]1[C:35]([O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:40])[CH3:41])=[C:34]2[C:30](=[C:29]([CH3:44])[C:28]=1[O:45][CH3:46])[CH2:31][O:32][C:33]2=[O:43])(=[O:11])[O:8][CH2:9][CH3:10])[CH3:7]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 670098846-(3-Bromomethyl-pent-2-enyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

生成物 1

HCID 72563633{1-Cyano-3-ethyl-5-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-pent-3-enyl}-phosphonic Acid Diethyl Ester収率 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of diethyl cyanomethylphosphonate (233 mg, 1.32 mmol) in THF (1 mL) was added a THF solution of sodium bis(trimethysilyl)amide (1.0 M, 1.21 mL, 1.21 mmol). After stirring for 30 minutes, the solution was added dropwise to a solution of 6-(3-bromomethyl-pent-2-enyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (100 mg, 0.22 mmol) in THF (1 mL). The resulting mixture was allowed to stir at room temperature overnight before saturated aqueous ammonium chloride was added. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to dryness. The residue was purified by preparative reverse-phase HPLC, affording 51 mg (42%) of the desired product.

後処理

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by preparative reverse-phase HPLC

出典と根拠

ORDレコード
ord-ca22cd4441b14d3193294ff1556e1eec
出典データセット
uspto-grants-2008_09
特許番号
US07429565B2

関連ノート

読み込み中…