Acetaldehyde → HCID 59783851, compound

HRID 718057Notes

Reaction equation

HRID 718057 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:27]([Sn](Cl)(Cl)CCCC)[CH2:28]CC.C(=O)C.C1([SiH3])C=CC=CC=1>C1COCC1>[CH2:27]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:25][CH:26]=1)=[O:16])[CH3:28]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 59783539HCID 59783539, compound

Product 1

HCID 59783851HCID 59783851, compoundYield 530%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of compound 112 (1.00 g, 2.89 mmol) in THF was added dibutyltin dichloride (0.175 g, 0.577 mmol) and acetaldehyde (1.182 g, 26.8 mmol) and the reaction mixture was stirred 15 minutes. Phenylsilane (0.375 g, 3.46 mmol) was added and the reaction mixture was stirred at room temperature 60 h then solvent evaporated. The resulting crude product was purified by Isco (80 g column, 10%-50%) to afford title compound 113 (1.145 g, 100%) as a yellowish oil. LRMS (ESI): (calc) 374.16. (found) 375.4 (MH)+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature 60 h
  2. customsolvent evaporated
  3. customThe resulting crude product was purified by Isco (80 g column, 10%-50%)

Sources & evidence

ORD record
ord-2328383d8c534870883c937c38c98203
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

Loading…