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

HRID 1444667
Notes
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Reaction equation

HRID 1444667 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
ParticipantsProcedureWorkupSources & 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-nitrothiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-(benzylthio)-5-nitrothien-3-yl]methanol (3.9g, 13.9 mmol) in dichloromethane (8 mL) was reacted with diisopropylethylamine (7.42 mL, 3 equivalents) 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-40m column eluting with dichloromethane to give 3-(benzylthio)-4-[(methoxymethoxy)methyl]-2-nitrothiophene as a yellowish oil, (4.32 g, 94%). 1H NMR (300 MHz, CDCl3) δ ppm 3.36 (s, 3H), 4.20 (s, 2H), 4.34 (s, 2H), 4.62 (s, 2H), 7.13 (m, 3H), 7.21 (m,2H), 7.40 (s, 1H)

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-40m column
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-06d6ebd7a0914190a5fbda698b509057
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07662958B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes