Tributylphosphine → HCID 69801593, compound

HRID 984309Notes

Reaction equation

HRID 984309 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[CH2:13][OH:14].C(P(CCCC)CCCC)CCC.[CH2:28]([O:30][C:31](=[O:44])[C@@H:32]([O:41][CH2:42][CH3:43])[CH2:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=1)[CH3:29].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[CH2:28]([O:30][C:31](=[O:44])[C@@H:32]([O:41][CH2:42][CH3:43])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:14][CH2:13]/[CH:12]=[CH:11]/[C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:36][CH:35]=1)[CH3:29]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 10679056HCID 10679056, compound

Product 1

HCID 69801593HCID 69801593, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Under an atmosphere of nitrogen, (E)-3-naphthalen-2-yl-prop-2-en-1-ol (190 mg, 0.8 mmol), tributylphosphine (323 mg, 1.6 mmol) and (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (184 mg, 1.0 mmol) were successively dissolved in dry benzene (20 mL). Solid 1,1′-(azodicarbonyl) dipiperidine (403 mg, 1.6 mmol) was added at 0° C. with stirring. After 10 min. the reaction was warmed to room temperature and the stirring continued for 1 h. The reaction mixture was concentrated in vacuo and the product purified by flash column chromatography, eluting with heptane/ethyl acetate (3:2), to give 180 mg (55%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product purified by flash column chromatography
  3. washeluting with heptane/ethyl acetate (3:2)

Sources & evidence

ORD record
ord-82e3f0e2f38243e9b718c8eef53812af
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

Loading…