Chloromethyl Methyl Ether → 4-Iodo-2-methoxy-3-methoxymethoxymethylpyridine

HRID 2086343Notes

Reaction equation

HRID 2086343 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10][OH:11].[CH2:12](Cl)[O:13][CH3:14].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10][O:11][CH2:12][O:13][CH3:14]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 11437022(4-Iodo-2-methoxy-pyridin-3-yl)methanol

Product 1

HCID 121154024-Iodo-2-methoxy-3-methoxymethoxymethylpyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure in Example 2, the reaction was carried out with 2b (1.77 g, 6.68 mmol), MOMCl (1.52 mL, 20 mmol) and iPr2EtN (3.49 mL, 20 mmol) in dry CH2Cl2 (40 mL) to afford 3b as an orange-yellow oil (2.06 g, 100%). The crude product was sufficiently pure for the subsequent reaction. IR (CH2Cl2, NaCl, cm−1) 2949, 1561, 1459, 1380, 1265, 1039, 741; 1H NMR (300 MHz, CDCl3) δ3.45 (s, 3H), 3.96 (s, 3H), 4.72 (s, 2H), 4.75 (s, 2H), 7.35 (d,J=5.4 Hz, 1H), 7.71 (d,J=5.4 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ54.35, 55.80, 67.89, 96.70, 114.20, 123.97, 128.10, 147.11, 162.39; HRMS (EI) m/z calcd for C9H12NO3I (M+) 308.9862, found 308.9860; LRMS (EI) m/z 309(M+, 19), 277(20), 264(45), 248(100), 218(68), 152(39), 92(50), 79(35).

Sources & evidence

ORD record
ord-9c174113935e47e0ab88ba2ee04898bd
Source dataset
uspto-grants-2004_04
Patent number
US06723853B2

Reaction notes

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