1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86607835, compound

HRID 646704Notes

Reaction equation

HRID 646704 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11](O)[CH2:10][CH2:9]2.C1(P([N:30]=[N+:31]=[N-:32])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OCC)(=O)C>[N:30]([CH:11]1[C:12]2[C:8](=[CH:7][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10]1)=[N+:31]=[N-:32]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 68651697HCID 68651697, compound

Product 1

HCID 86607835HCID 86607835, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2-thienyl)-2,3-dihydro-1H-inden-1-ol (0.30 g, 1.39 mmol) in tetrahydrofuran (6 mL ) was added diphenylphosphoryl azide (0.58 g, 2.10 mmol) at 0° C. The reaction was stirred for 5 min prior to the addition of 1,8-diazabicyclo{5.4.0]undec-7-ene (DBU, 0.32 g, 2.10 mmol). The reaction was further stirred for 15 min at 0° C. before the reaction was allowed to warm to room temperature. The reaction was stopped after 1 h when the reaction was completed as monitored by thin layer chromatography. Diluted with ethyl acetate (200 mL), washed with water, saturated aqueous sodium chloride (brine), and dried over anhydrous magnesium sulfate. Filtration, concentration and column chromatography on silica (7:3 hexanes/ethyl acetate) gave 2-(1-azido-2,3-dihydro-1H-indene-5-yl)thiophene (0.24g, 72% yield) as oil. 1H NMR (400 MHz, CDCl3) 7.54 (m, 2H), 7.40 (m, 2H), 7.24 (m, 1H), 7.08 (m, 1H), 5.85 (t, 1H), 3.12 (m, 1H), 2.90 (m, 1H), 2.45 (m, 1H), 2.19 (m, 1H).

Workup

  1. stirringThe reaction was further stirred for 15 min at 0° C. before the reaction
  2. waitThe reaction was stopped after 1 h
  3. washwashed with water, saturated aqueous sodium chloride (brine)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration, concentration and column chromatography on silica (7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-8ac7068c42fe42e0af33dd31898d30af
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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