Acetaldehyde → 3-(5-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

HRID 1263721ノート

反応式

HRID 1263721 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2.[CH:21](=O)[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:21]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2)[CH3:22]

参加物

4

反応物 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 696596273-(5-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

生成物 1

HCID 696602193-(5-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one収率 25.5%

実験手順

A mixture of 3-(5-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (50.0 mg, 0.189 mmol), acetaldehyde (10.0 mg, 0.227 mmol), and sodium triacetoxyborohydride (52.1 mg, 0.246 mmol) was stirred at room temperature for 50.5 h. The reaction was then partitioned between EtOAc and H2O. The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the solid chromatographed (CHCl3/MeOH, 97.5:2.5) to afford the title compound (14.1 mg, 25%) as a yellow solid.

後処理

  1. customThe reaction was then partitioned between EtOAc and H2O
  2. washThe organic phase was washed with H2O, brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe solid chromatographed (CHCl3/MeOH, 97.5:2.5)

出典と根拠

ORDレコード
ord-eb2da858b2e94e35bcc7e211778baf6c
出典データセット
uspto-grants-2003_04
特許番号
US06541504B1

反応ノート

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