Tin tetrachloride → (E)-1-ethoxy-9,11-dimethylazacycloundec-8-en-2-one

HRID 2205258Notes

Reaction equation

HRID 2205258 reaction equation
[CH2:1]=[C:2]([CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:11])[CH3:3].[CH2:12]([O:14][N:15]=[CH:16][CH3:17])[CH3:13].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH2:12]([O:14][N:15]1[CH:16]([CH3:17])[CH2:3][C:2]([CH3:1])=[CH:4][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:11])[CH3:13]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 533741acetaldehyde O-ethyl oximeHCID 714262142-(Prop-1-en-2-yl)cycloheptanone

Product 1

HCID 131735806(E)-1-ethoxy-9,11-dimethylazacycloundec-8-en-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Following the general procedure as described in Example 17, 2-(prop-1-en-2-yl)cycloheptanone (0.97 g, 6.38 mmol), acetaldehyde O-ethyl oxime (0.66 g, 7.65 mmol), and SnCl4 (1.66 g, 6.38 mmol) in 1,2-dichloroethane (65 ml) were reacted to give the title product as a colorless liquid (1.11 g, 73% yield).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0142ca6cf3624a1a9003d2d1f04269f3
Source dataset
uspto-grants-2016_06
Patent number
US09371262B2

Reaction notes

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