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

HRID 2205262Notes

Reaction equation

HRID 2205262 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].[CH3:17][O:18][N:19]=[CH:20][CH3:21].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH3:17][O:18][N:19]1[CH:20]([CH3:21])[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]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 535486Acetaldehyde, O-methyloximeHCID 135824482-(Prop-1-en-2-yl)cyclododecanone

Product 1

HCID 131735808(E)-1-methoxy-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-methyl oxime (0.99 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 (2.33 g, 88% yield). Mixture of E/Z isomers in a ratio of 3:1.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9690829cff574137975a50019cc3aa1a
Source dataset
uspto-grants-2016_06
Patent number
US09371262B2

Reaction notes

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