Acetaldehyde → HCID 178468173, compound

HRID 1968966Notes

Reaction equation

HRID 1968966 reaction equation
[CH:1](=[O:3])[CH3:2].[Si](O[C@H:12]1[CH2:17][CH2:16][C@H:15]([N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])[CH2:14][CH2:13]1)(C(C)(C)C)(C)C.[Bi](Br)(Br)Br.C([SiH](CC)CC)C>C(#N)C>[CH2:1]([O:3][C@H:12]1[CH2:13][CH2:14][C@H:15]([N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])[CH2:16][CH2:17]1)[CH3:2]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 12052TriethylsilaneHCID 82232bismuth(III) bromideHCID 178455354HCID 178455354, compound

Product 1

HCID 178468173HCID 178468173, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Acetaldehyde (10 mL; 0.17 mol) in acetonitrile (50 mL) was added over 30 minutes to a solution of trans-N-(4-tert-butyldimethylsilyloxycyclohexyl)phthalimide (D63; 50.0 g; 0.14 mol), bismuth tribromide (6.7 g; 0.015 mol) and triethylsilane (27 mL; 0.18 mol) in acetonitrile (500 mL) stirred at ice bath temperature and the mixture was allowed to warm to room temperature overnight. The mixture was filtered and the resulting grey solid and filtrate were worked up separately. The filtrate was evaporated and treated with hexane to give the title compound as a white solid (16.35 g). The grey solid was washed with dichloromethane, the dichloromethane extract was evaporated and the residue was stirred with hexane (200 mL) to give a second crop of the title compound as a white solid (17.47 g).

Workup

  1. filtrationThe mixture was filtered
  2. customThe filtrate was evaporated
  3. additiontreated with hexane

Sources & evidence

ORD record
ord-5ee7cced5d4743fe973446b094c5cbf9
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

Loading…