Trityl chloride → Methyl 6-trityloxy-hexanoate

HRID 467388

Reaction equation

HRID 467388 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 67198977Methyl 6-trityloxy-hexanoateYield 86.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-6531ea321f00422ebe5aa2db57165381
Source dataset
uspto-grants-2014_01
Patent number
US08623326B2

Linked notes

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