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

HRID 2041237Notes

Reaction equation

HRID 2041237 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-747391e2d7cf44eeb50a35f1aeb625ab
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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