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

HRID 494469
Notes
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Reaction equation

HRID 494469 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-10840c56f1fd4cd3a86663d614fb5285
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538105B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes