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

HRID 2224790
Notes
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Reaction equation

HRID 2224790 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of the product of Example 10B (3.9 g, 13.9 mmol) and diisopropylethylamine (7.42 mL, 43 mmol) in dichloromethane (8 mL) was treated with methoxymethyl chloride (2.38 mL, 32 mmol), stirred at 25° C. for 16 hours. The mixture was concentrated in vacuo and the residue was chromatographed on silica gel, eluting with dichloromethane to give the title compound (4.32 g, 94%). 1H NMR (300 MHz, CDCl3): δ 7.40 (s, 1 H), 7.21 (m, 2 H), 7.13 (m, 3 H), 4.62 (s, 2 H), 4.34 (s, 2 H), 4.20 (s, 2 H), 3.36 (s, 3 H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-b43b9708002b4b44ba14655d6bd82520
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07378414B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes