Oxalyl chloride → (6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester

HRID 250269

反応式

HRID 250269 の反応式
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].[CH3:24][O-:25].[Na+]>C(OCC)C>[CH3:24][O:25][C:18](=[O:22])[C:19]([C:13]1[C:12]2[C:16](=[CH:17][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[NH:15][CH:14]=1)=[O:20]

参加物

5

反応物 3

HCID 65578Oxalyl chlorideHCID 2608046-(benzyloxy)-1H-indoleHCID 10942334Sodium Methoxide

生成物 1

HCID 34181007(6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester収率 95%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A 0° C. solution of 6-benzyloxyindole (2.10 g, 9.41 mmol) in diethyl ether (20 mL) is treated with oxalyl chloride (1.02 mL, 11.8 mmol). The mixture is stirred for 2 hours while warming to room temperature. The mixture is cooled to −78° C. and sodium methoxide (5.41 mL, 4.35 M) is added. The mixture is warmed up to room temperature over 20 minutes and the reaction is quenched with water (10 mL). The resulting mixture is filtered to obtain the title compound (2.75 g, 95%) as a yellow solid. ES/MS m/e 310.0 (M+1), 308.0 (M−1).

後処理

  1. temperatureThe mixture is cooled to −78° C.
  2. temperatureThe mixture is warmed up to room temperature over 20 minutes
  3. customthe reaction is quenched with water (10 mL)
  4. filtrationThe resulting mixture is filtered

出典と根拠

ORDレコード
ord-aa1e9d45db704aaebbfd52b753169a8b
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

関連ノート

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