Tributylphosphine → HCID 9913001, compound

HRID 323594Notes

Reaction equation

HRID 323594 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH2:5][CH2:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH:9]([O:12][CH2:13][CH2:14][OH:15])[C:10]=2[N:11]=1.C(P(CCCC)CCCC)CCC.[CH2:33]([O:35][C:36](=[O:49])[CH:37]([O:46][CH2:47][CH3:48])[CH2:38][C:39]1[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=1)[CH3:34].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1C=CC=CC=1.O>[CH2:33]([O:35][C:36](=[O:49])[CH:37]([O:46][CH2:47][CH3:48])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:15][CH2:14][CH2:13][O:12][CH:9]2[C:8]3[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=3[CH2:6][CH2:5][C:4]3[O:3][C:2]([CH3:1])=[N:11][C:10]2=3)=[CH:41][CH:40]=1)[CH3:34]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 22727927HCID 22727927, compound

Product 1

HCID 9913001HCID 9913001, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 2-(2-methyl-9,10-dihydro-4H-1-oxa-3-aza-benzo[f]azulen-4-yloxy)-ethanol (400 mg, 1.6 mmol), tributylphosphine (480 mg, 2.4 mmol) and 2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (380 mg, 1.6 mmol) were successively dissolved in dry benzene (10 mL). Solid azodicarboxylic dipiperidine (ADDP) (480 mg, 2.4 mmol) was added under stirring at 0° C. to the solution. After 10 min, the reaction mixture was brought to room temperature and the stirring was continued for 16 h. The mixture was added water and the product extracted with ethyl acetate. The combined organic phases was dried (MgSO4), and concentrated in vacuo. The residue was purified chromatography eluting with petroleum ether/ethyl acetate (1:1) to give 300 mg (40%) of the title compound: 1H NMR (300 MHz, CDCl3) δ1.15 (t, 3H). 1.20 (t, 3H), 22.38 (s, 3H), 2.60-2.85 (m, 2H), 2.90-3.05 (m, 3H), 3.25-3.38 (m, 1H), 3.52-3.65 (m, 1H), 3.65-3.75 (m, 1H). 3.75-3.90 (m, 2H), 3.95 (t, 1H), 4.05 (t, 2H), 4.15 (q, 2H), 5.25 (s, 1H), 6.75 (d, 2H), 7.10 (d, 2H), 7.13-7.30 (m, 4H).

Workup

  1. customwas brought to room temperature
  2. waitthe stirring was continued for 16 h
  3. extractionthe product extracted with ethyl acetate
  4. dry with materialThe combined organic phases was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified chromatography
  7. washeluting with petroleum ether/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-df404f5f3a7e43d89a3f9f8855518300
Source dataset
uspto-grants-2001_04
Patent number
US06214820B1

Reaction notes

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