Water → 3-(4-(2-[5H-Dibenzo[a,d]cyclohepten-5-yloxy)-ethoxy]-phenyl)-2-ethoxy-propionic acid ethyl ester

HRID 394628Notes

Reaction equation

HRID 394628 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([O:16][CH2:17][CH2:18][OH:19])[C:5]=2[CH:4]=[CH:3][CH:2]=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].O>C1C=CC=CC=1>[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:19][CH2:18][CH2:17][O:16][CH:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[CH:41][CH:40]=1)[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 13831TributylphosphineHCID 100835672-(5H-dibenzo[a,d]cyclohepten-5-yloxy)-ethanolHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 99345053-(4-(2-[5H-Dibenzo[a,d]cyclohepten-5-yloxy)-ethoxy]-phenyl)-2-ethoxy-propionic acid ethyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 2-(5H-dibenzo[a,d]cyclohepten-5-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 2 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 ethyl acetate/hexane (1:9) to give 350 mg (47%) of the title compound: MS 472 (M+).

Workup

  1. customwas brought to room temperature
  2. waitthe stirring was continued for 2 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 ethyl acetate/hexane (1:9)

Sources & evidence

ORD record
ord-f1f52752306c4e018411a2f07f452c64
Source dataset
uspto-grants-2003_08
Patent number
US06602901B2

Reaction notes

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