Tin tetrachloride → (E)-1-ethoxy-14,16-dimethylazacyclohexadec-13-en-2-one

HRID 2205263Notes

Reaction equation

HRID 2205263 reaction equation
[CH2:1]=[C:2]([CH:4]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:16])[CH3:3].[CH2:17]([O:19][N:20]=[CH:21][CH3:22])[CH3:18].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH2:17]([O:19][N:20]1[CH:21]([CH3:22])[CH2:3][C:2]([CH3:1])=[CH:4][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:16])[CH3:18]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 533741acetaldehyde O-ethyl oximeHCID 135824482-(Prop-1-en-2-yl)cyclododecanone

Product 1

HCID 89525732(E)-1-ethoxy-14,16-dimethylazacyclohexadec-13-en-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Following the general procedure as described in Example 23, 2-(prop-1-en-2-yl)cyclododecanone (2.00 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 (2.45 g, 88% yield). Mixture of E/Z isomers in a ratio of 2:1.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4541ebd2587e4fabb0c5b78936cd4e9c
Source dataset
uspto-grants-2016_06
Patent number
US09371262B2

Reaction notes

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