Azide → HCID 57443977, compound

HRID 1172859Notes

Reaction equation

HRID 1172859 reaction equation
O[CH:2]([C:4]1[CH:17]=[CH:16][C:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:6]=2[CH:5]=1)[CH3:3].C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1.[N-]=[N+]=[N-]>C1(C)C=CC=CC=1>[N:32]([CH:2]([C:4]1[CH:17]=[CH:16][C:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:6]=2[CH:5]=1)[CH3:3])=[N+:33]=[N-:34]

Participants

6

Reactant 4

HCID 33558AzideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 199401P,P-Diphenylphosphinic azideHCID 57443976HCID 57443976, compound

Product 1

HCID 57443977HCID 57443977, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 6-(1-hydroxyethyl)-1-benzothiophene-2-carboxylate (2.0 g, 8.06 mmol) in toluene (30 mL) was added diphenylphosphorylazide (2.64 g, 9.58 mmol), then DBU (1.31 mL, 8.79 mmol) dropwise. After 24 h, added more azide (0.5 mL) and DBU (0.3 mL) to the thick solution. After an additional 24 h, the reaction mixture was concentrated and purified via column chromatography yielding the desired product. 1H NMR (CDCl3, 600 MHz) δ 8.03 (d, J=0.9 Hz, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.81 (m, 1H), 7.36 (dd, J=8.2, 0.9 Hz, 1H), 4.75 (q, J=6.8 Hz, 1H), 4.40 (q, J=7.3 Hz, 2H), 1.58 (d, J=6.8 Hz, 3H), 1.41 (t, J=7.3 Hz, 3H). MS: cal'd 276 (MH+), exp 276 (MH+).

Workup

  1. waitAfter an additional 24 h
  2. concentrationthe reaction mixture was concentrated
  3. custompurified via column chromatography

Sources & evidence

ORD record
ord-4993f8b8c5e341b08100cee5f89d5285
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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