Water → Propargyl-PEG3-NH2

HRID 1844291Notes

Reaction equation

HRID 1844291 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][C:14]#[CH:15])=[N+]=[N-].O.[Na+].[Cl-].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][C:14]#[CH:15]

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 57871935HCID 57871935, compound

Product 1

HCID 57871953Propargyl-PEG3-NH2

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 11776TriphenylphosphineSolvent

Procedure

in a 50 mL flask, 3 (150 mg, 0.7 mmol), Ph3P were dissolved in 10 mL THF. The reaction mixture was stirred at rt for 3 hr. To the reaction mixture was added H2O (1 mL) the resultant mixture was stirred for 36 hr at rt. The solvent was evaporated and the residue was purified by FCC to afford 4 as slightly yellow oil (131 mg, quant.). 1H NMR (400 MHz, CDCl3): δ 1.46 (br, 2H), 2.35 (t, J=1.6 Hz, 1H), 2.73 (t, J=5.2 Hz, 2H), 3.38 (t, J=5.2 Hz, 2H) 3.50-3.59 (m, 10H), 4.08 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 41.72, 58.34, 69.04, 70.21, 70.36, 70.54, 73.36, 74.63, 79.60. ESIMS calcd for C9H18NO3 [M+H]+ 188.13, found: 188.16. FTIR (NaCl plate, CH2Cl2): 1118 (C—O str), 2111 (C≡C str), 2869 (C—H str), 3249 (N—H str).

Workup

  1. stirringwas stirred for 36 hr at rt
  2. customThe solvent was evaporated
  3. customthe residue was purified by FCC
  4. customto afford 4 as slightly yellow oil (131 mg, quant.)

Sources & evidence

ORD record
ord-2e917de7febf4affbd95abe51dace6a2
Source dataset
uspto-grants-2015_02
Patent number
US08946391B2

Reaction notes

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