Chloromethyl Methyl Ether → 3-(Benzylthio)-4-[(methoxymethoxy)methyl]-2-nitrothiophene

HRID 601293Notes

Reaction equation

HRID 601293 reaction equation
[CH2:1]([S:8][C:9]1[C:10]([CH2:17][OH:18])=[CH:11][S:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:28][O:29][CH2:30]Cl>ClCCl>[CH2:1]([S:8][C:9]1[C:10]([CH2:17][O:18][CH2:28][O:29][CH3:30])=[CH:11][S:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 59168797(4-Benzylsulfanyl-5-nitro-thiophen-3-yl)-methanol

Product 1

HCID 670638303-(Benzylthio)-4-[(methoxymethoxy)methyl]-2-nitrothiopheneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 309D (3.9 g, 13.9 mmol) in dichloromethane (8 mL) was reacted with diisopropylethylamine (7.42 mL, 3 equivivalents) and methoxymethyl chloride (2.38 mL, 2.25 equivalents) at 25° C. 16 hours. The reaction was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel using a Biotage-40 m column eluting with dichloromethane to give the title compound as a yellowish oil, (4.32 g, 94%). 1H NMR (300 MHz, CDCl3) δ ppm 3.36 (s, 3 H), 4.20 (s, 2 H), 4.34 (s, 2 H), 4.62 (s, 2 H), 7.13 (m, 3 H), 7.21 (m, 2 H), 7.40 (s, 1 H).

Workup

  1. custom16 hours
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe residue purified by flash chromatography on silica gel using a Biotage-40 m column
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6801e9cb34d9458198b7e2000f6e6802
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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