Crotonaldehyde → HCID 86708058, compound

HRID 1524357Notes

Reaction equation

HRID 1524357 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([C@@H:25]([CH2:35][CH:36]=[CH2:37])[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:18])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:38](=[O:42])/C=C/C>ClCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([C@@H:25]([CH2:35]/[CH:36]=[CH:37]/[CH:38]=[O:42])[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:18])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 447466CrotonaldehydeHCID 86708059HCID 86708059, compound

Product 1

HCID 86708058HCID 86708058, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the material from Step 3 (9.5 g, 16.67 mmol) and crotonaldehyde (6.90 mL, 83 mmol) in dichloromethane (183 mL) was heated at reflux. Grubbs' 2nd Generation catalyst (0.71 g, 0.833 mmol) was added, and the reaction mixture was stirred at reflux for 4 hours. The reaction mixture was concentrated to dryness in vacuo and the residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 7.4 g of the title compound. LCMS (M+Na)=620.

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated to dryness in vacuo
  4. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f71f6a7a1a51410bb03c597401b08807
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

Loading…