4-Methoxybenzyl alcohol → HCID 70497530, compound

HRID 333647

Reaction equation

HRID 333647 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[Cl:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:53][O:54][C:55]1[CH:62]=[CH:61][C:58]([CH2:59]O)=[CH:57][CH:56]=1>C1COCC1>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([O:20][CH2:59][C:58]2[CH:61]=[CH:62][C:55]([O:54][CH3:53])=[CH:56][CH:57]=2)=[O:19])[C:3]=1[Cl:21]

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 25181547Halauxifen

Product 1

HCID 70497530HCID 70497530, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinic acid (600 mg, 1.81 mmol) in THF (10 mL) was added triphenylphosphine (475 mg, 1.81 mmol), diethyl azodicarboxylate (0.29 mL, 1.81 mmol), and 4-methoxybenzyl alcohol (0.34 mL, 2.72 mmol). The reaction mixture was stirred for 48 h. Additional triphenylphosphine (475 mg, 1.81 mmol) was added to the reaction, and the reaction mixture was stirred for 24 h. The reaction mixture was concentrated to dryness and was purified by silica gel chromatography (eluting with a 0-100% EtOAc/hexane gradient) to provide an off-white solid (170 mg, 26%): mp 73-83° C.; 1H NMR (400 MHz, CDCl3) δ 7.66 (dd, J=8.6, 7.8 Hz, 1H), 7.45-7.38 (m, 2H), 7.22 (dd, J=8.7, 1.8 Hz, 1H), 7.16 (d, J=1.7 Hz, 1H), 6.94-6.87 (m, 2H), 5.38 (s, 2H), 4.80 (s, 2H), 3.96 (d, J=0.8 Hz, 3H), 3.81 (s, 3H); ESIMS m/z 451 ([M+H]+), 449 ([M−H]−).

Workup

  1. stirringthe reaction mixture was stirred for 24 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customwas purified by silica gel chromatography (
  4. washeluting with a 0-100% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-567ecb0ca2894d9e944c5c3a8e11737f
Source dataset
uspto-grants-2014_11
Patent number
US08883688B2

Linked notes

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