Trityl chloride → Methyl-12-trityloxy-dodecanoate

HRID 467389

Reaktionsgleichung

Reaktionsgleichung von HRID 467389
[C:1]([O:20][CH2:21][CH2:22]CCCC(OC)=O)([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.C(Cl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:50][O:51][C:52](=[O:65])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61]CCO>N1C=CC=CC=1>[CH3:50][O:51][C:52](=[O:65])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:22][CH2:21][O:20][C:1]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 522424Methyl 12-hydroxydodecanoateHCID 67198977Methyl 6-trityloxy-hexanoate

Produkt 1

HCID 67200799Methyl-12-trityloxy-dodecanoateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

The synthesis procedure of 15a was followed. Trityl chloride (1412 mg, 5.1 mmol), 14c (583 mg, 2.5 mmol), and pyridine (10 mL) were used and the reaction was prolonged to 3 days. The filtration step was omitted, instead the crude material was purified by flash column chromatography (10% EtOAc in hexanes) yielding 477 mg (40%) of a pale yellow oil 15c. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.44 (6H, m, p-Ar), 7.28 (6H, m, m-Ar), 7.21 (3H, m, o-Ar), 3.66 (3H, s, CO2CH3), 3.03 (2H, t, 3JH—H=6.6 Hz, H)—CH2), 2.29 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.55-1.65 (4H, m, 2CH2), 1.10-1.39 (14H, m, 7CH2). HRMS (EI): m/z calcd 472.2977 (C32H40O3), found 472.2968 [M]+.

Aufarbeitung

  1. filtrationThe filtration step
  2. custominstead the crude material was purified by flash column chromatography (10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-97903a68f3f54b51a3bbcb210323c15d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623326B2

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