Tin tetrachloride → (E)-1-ethoxy-10,12-dimethylazacyclododec-9-en-2-one

HRID 2205261Notes

Reaction equation

HRID 2205261 reaction equation
[CH2:1]=[C:2]([CH:4]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:12])[CH3:3].[CH2:13]([O:15][N:16]=[CH:17][CH3:18])[CH3:14].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH2:13]([O:15][N:16]1[CH:17]([CH3:18])[CH2:3][C:2]([CH3:1])=[CH:4][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:12])[CH3:14]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 533741acetaldehyde O-ethyl oximeHCID 895256422-(Prop-1-en-2-yl)cyclooctanone

Product 1

HCID 89526188(E)-1-ethoxy-10,12-dimethylazacyclododec-9-en-2-oneYield 87%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Following the general procedure as described in Example 23, 2-(prop-1-en-2-yl)cyclooctanone (1.50 g, 9.02 mmol), acetaldehyde O-ethyl oxime (1.18 g, 13.53 mmol), and SnCl4 (2.35 g, 9.02 mmol) in 1,2-dichloroethane (90 ml) were reacted to give the title product as a colorless liquid (1.98 g, 87% yield). E isomer>96%.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4d123007867f4764897cf564709291dc
Source dataset
uspto-grants-2016_06
Patent number
US09371262B2

Reaction notes

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