Acetaldehyde → HCID 59783851, compound

HRID 1946590Notes

Reaction equation

HRID 1946590 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-b165a8854ea44ee5a55770890dd8c5aa
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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