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Pyridine → 3-Phenylpropyl carbonochloridate

HRID 530470
Notes
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Reaction equation

HRID 530470 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[C:19]1([CH2:25][CH2:26][CH2:27][OH:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:19]1([CH2:25][CH2:26][CH2:27][O:28][C:2]([Cl:1])=[O:4])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 31234BenzenepropanolHCID 94429Triphosgene

Product 1

HCID 214186893-Phenylpropyl carbonochloridateYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

In a four necked round bottom flask, triphosgene (5.45 g, 55.1 mmol) was dissolved in toluene (80 mL) under argon. After cooling at 0° C., pyridine (4.8 mL, 58.8 mmol) was added dropwise during 1 h and the resulting suspension stirred for further 1 h at 0° C. 3-phenyl-1-propanol (5 mL, 36.8 mmol) was added dropwise in 30 min. After stirring at rt for 24 h, the solid was filtered off and the solvent removed under vacuum, yielding the title compound (6.2 g, 85%) as pale yellow oil, which was used in the next step without further purification. FTIR (cm−1): 3086, 3065, 3027, 2995, 2932, 2862, 1776, 1743, 1603, 1496, 1454, 1262, 1148, 745, 699.

Workup

  1. stirringAfter stirring at rt for 24 h
  2. filtrationthe solid was filtered off
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-831f1103789645beb64d32149917cc55
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09353075B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes