Acetaldehyde → HCID 178468173, compound

HRID 2060011Notes

Reaction equation

HRID 2060011 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-3c3a7d8bdca0421cbdb6dd9fcd1ba788
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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