Trityl chloride → Methyl 6-trityloxy-hexanoate

HRID 467388

반응식

HRID 467388 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 67198977Methyl 6-trityloxy-hexanoate수율 86.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-6531ea321f00422ebe5aa2db57165381
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623326B2

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