1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(1-Azidoethyl)-5-methylthiophene

HRID 911349Notes

Reaction equation

HRID 911349 reaction equation
C1CCN2C(=NCCC2)CC1.O[CH:13]([C:15]1[S:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[CH3:14].C1(P([N:35]=[N+:36]=[N-:37])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:35]([CH:13]([C:15]1[S:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[CH3:14])=[N+:36]=[N-:37]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 150917951-(5-Methyl-2-thienyl)ethanol

Product 1

HCID 576559232-(1-Azidoethyl)-5-methylthiopheneYield 78%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add DBU (1.228 g, 1.2 mL, 8.07 mmol) to a solution of (−)-2-(1-hydroxyethyl)-5-methylthiophene (0.955 g, 6.72 mmol) and diphenylphosphoryl azide (2.22 g, 1.74 mL, 8.07 mmol) in anhydrous toluene. Stir at room temperature for 18 h. Dilute the mixture with EtOAc and wash with water and 0.5N aqueous HCl. Dry the organic phase over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 19:1) to obtain the desired intermediate as an oil (0.875 g, 78%). GC-MS m/z 167 (M+).

Workup

  1. washwash with water and 0.5N aqueous HCl
  2. dry with materialDry the organic phase over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 19:1)

Sources & evidence

ORD record
ord-3be3c845cb574a16b0741bdd8be86d3e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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