Cinnamoylbenzene → HCID 13053439, compound

HRID 2235824Notes

Reaction equation

HRID 2235824 reaction equation
[Li]CCCC.[S:6]1[CH2:11][CH2:10][CH2:9][S:8][CH2:7]1.[C:12]1([CH:18]=[CH:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[S:6]1[CH2:11][CH2:10][CH2:9][S:8][CH:7]1[CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]

Participants

5

Reactant 3

HCID 7189CinnamoylbenzeneHCID 104511,3-DithianeHCID 178418339Butyllithium

Product 1

HCID 13053439HCID 13053439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

n-BuLi (2.5 M in hexanes; 7.50 mL; 18.8 mmol) was added over 2 min to [1,3]dithiane (1.876 g; 15.6 mmol) in dry THF (20 mL) at −78° C. The r×n warmed to −20° C. over 1.5 h then was cooled to −78° C. and chalcone (3.239 g; 15.6 mmol) was added in one portion. After 6 h the r×n was quenched with satd NH4Cl. Aq/organic extractions were followed by partial purification by MPLC (silica eluting with a dichloromethane in hexanes gradient) affording a mixture of [1,2] and [1,4] addition products. 1H NMR (CDCl3; partial spectrum for major product) δ 4.38 (d, J=6.8 Hz, 1H), 3.50 (dd, J=8.2, 17.4 Hz, 1H).

Workup

  1. temperaturethen was cooled to −78° C.
  2. customAfter 6 h the r×n was quenched with satd NH4Cl
  3. extractionAq/organic extractions
  4. customwere followed by partial purification by MPLC (silica eluting with a dichloromethane in hexanes gradient)
  5. customaffording

Sources & evidence

ORD record
ord-b8ba56868b254f4584ada6dda4fc35f7
Source dataset
uspto-grants-2010_05
Patent number
US07714022B2

Reaction notes

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