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

HRID 250269

반응식

HRID 250269 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aa1e9d45db704aaebbfd52b753169a8b
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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