Triphenylphosphine → HCID 10922629, compound

HRID 354473Notes

Reaction equation

HRID 354473 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].C([NH:22][CH2:23][CH2:24]O)(OC(C)(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:14][O:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[O:1][CH2:24][CH2:23][NH2:22])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 12038Ethyl vanillateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 10922629HCID 10922629, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-hydroxy-3-methoxybenzoate (1.46 g, 7.44 mmol), N-Boc ethanolamine (1.19 g, 7.38 mmol), PPh3 (2.53 g, 9.65 mmol) in THF (30 mL) was added DIAD (1.90 mL, 9.65 mmol), and the resulting mixture was then heated under reflux overnight. The mixture was evaporated to give a crude gum. The crude product was dissolved in CH2Cl2 (20 mL) and TFA (20 mL). The resulting mixture was stirred for 2.5 hr at room temp. The mixture was concentrated in vacuo and the residue was made basic with sat. NaHCO3 and extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and evaporated to give the 1.61 g (90% for 2 steps ) ethyl 3-methoxy-4-(2-aminoethoxy)benzoate as a yellow oil. 1H-NMR (CDCl3) d 1.39 (t, 3 H, J=7.3 Hz), 3.14-3.17 (m, 2 H), 3.92 (s, 3 H), 4.09-4.11 (m, 2 H), 4.36 (q, 2 H, J=7.3 Hz), 6.89 (d, 1 H, J=8.3 Hz), 7.56 (d, 1 H, J=2.0 Hz), 7.66 (dd, 1 H, J=2.0, 8.3 Hz).

Workup

  1. temperaturethe resulting mixture was then heated
  2. temperatureunder reflux overnight
  3. customThe mixture was evaporated
  4. customto give a crude gum
  5. concentrationThe mixture was concentrated in vacuo
  6. extractionextracted with CHCl3
  7. washThe extract was washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-052184a95ec7466b888d194ed108584d
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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