Trityl chloride → Methyl 6-trityloxy-hexanoate

HRID 467388

反応式

HRID 467388 の反応式
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28]>N1C=CC=CC=1>[C:1]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 6456Trityl chlorideHCID 3083855Hexanoic acid, 6-hydroxy-, methyl ester

生成物 1

HCID 67198977Methyl 6-trityloxy-hexanoate収率 86.3%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Trityl chloride (18.8 g, 67.4 mmol) was added to an ice cold (0° C.) stirring solution of 14a (9.9 g, 67.4 mmol) in 80 mL of pyridine. The reaction mixture was warmed to room temperature and stirred under argon for 2 days, during which time a white byproduct formed. The solvent was removed under reduced pressure, and the resulting material was redissolved in ice cold THF. The insoluble byproduct was removed by filtration, and the filtrate was dried under reduced pressure to obtain 22.6 g (86%) of an orange oil 15a. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.29 (6, m, m-Ar), 7.22 (3H, m, o-Ar), 3.65 (3H, s, CO2CH3), 3.05 (2H, t, 3JH—H=6.6 Hz, HO—CH2), 2.29 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.54-1.71 (4H, m, 2CH2), 1.33-1.45 (m, 2H, CH2). HRMS (EI): m/z calcd 388.2038 (C26H28O3), found 388.2039 [M]+.

後処理

  1. customformed
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe resulting material was redissolved in ice cold THF
  4. customThe insoluble byproduct was removed by filtration
  5. customthe filtrate was dried under reduced pressure

出典と根拠

ORDレコード
ord-6531ea321f00422ebe5aa2db57165381
出典データセット
uspto-grants-2014_01
特許番号
US08623326B2

関連ノート

読み込み中…