Water → HCID 18182564, compound

HRID 1359589Notes

Reaction equation

HRID 1359589 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[NH2:1][CH2:4][CH2:5][CH:6]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18182534HCID 18182534, compound

Product 1

HCID 18182564HCID 18182564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-azido-ethyl)-5-cyano-2,3-dihydro-benzofuran (434 mg, 2 mmol) (reference example 7) in THF (10 mL) was added Ph3P (576 mg, 2.2 mmol). The resulting solution was stirred for 7 hr then H2O added (72 ml, 4 mmol). This solution was stirred for 18 hr then concentrated. The residue was azeotroped with toluene then used without further purification. 1H NMR (CDCl3) d 1.81 (m, 1H), 1.93 (m, 1H) 2.5 (bs, 2H), 2.81 (m, 2H), 3.60 (m, 1H), 4.32 (dd, J=8, 6 Hz, 1H), 4.73 (t, J=8 Hz, 1H) 6.83 (d, J=8 Hz, 1H), 7.46 (m, 2H).

Workup

  1. stirringThis solution was stirred for 18 hr
  2. concentrationthen concentrated
  3. customThe residue was azeotroped with toluene
  4. customthen used without further purification

Sources & evidence

ORD record
ord-56230f443d9343c2bad97d200fc673c3
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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