Trityl chloride → Methyl-12-trityloxy-dodecanoate

HRID 467389

Reaction equation

HRID 467389 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 67200799Methyl-12-trityloxy-dodecanoateYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-97903a68f3f54b51a3bbcb210323c15d
Source dataset
uspto-grants-2014_01
Patent number
US08623326B2

Linked notes

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