Sodium Hydroxide → N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic Acid

HRID 1610925ノート

反応式

HRID 1610925 の反応式
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20]C(=O)C)=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([O:26]CC)=[O:25])=[CH:6][C:5]=1[C:29]#[C:30][Si](C)(C)C>CO.O.C(OCC)(=O)C.CCCC(C)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([OH:26])=[O:25])=[CH:6][C:5]=1[CH2:29][CH3:30]

参加物

7

反応物 2

HCID 14798Sodium HydroxideHCID 22259369ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate

生成物 1

HCID 22259372N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic Acid収率 65.9%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 78922-Methylpentane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydroxide (2M, 1.8 ml) was added to a solution of ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate (0.14 g) in methanol (5 ml) and the mixture was stirred for 3 hours. The methanol was removed and the residue obtained was diluted with water (20 ml) and extracted twice with ethyl acetate (20 ml each time). The aqueous layer was acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (3×25 ml). The combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml) and dried (MgSO4). The residue obtained on removal of the solvent was dissolved in a mixture of ethyl acetate and iso-hexane (1:1) and passed down a 5 g silica Isolute column eluting with an ethyl acetate iso-hexane mixture (1:1) to give the title compound (65 mg). NMR (CD3SOCD3): d 4.5 (s, 1H), 5.7 (s, 2H), 6.8 (m, 1H), 6.9 (m, 2H), 7.1 (m, 1H), 7.2 (s, 1H), 7.35 (m, 1H), 7.4 (m, 2H), 9.0 (s, 1H); m/z 324.4 (M−H).

後処理

  1. customThe methanol was removed
  2. customthe residue obtained
  3. extractionextracted twice with ethyl acetate (20 ml each time)
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. washThe combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. customThe residue obtained on removal of the solvent
  8. washeluting with an ethyl acetate iso-hexane mixture (1:1)

出典と根拠

ORDレコード
ord-51ca09b46412458fae7bb2a7028d19d0
出典データセット
uspto-grants-2006_01
特許番号
US06984657B1

反応ノート

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