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

HRID 2205257Notes

Reaction equation

HRID 2205257 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].[CH3:12][O:13][N:14]=[CH:15][CH3:16].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH3:12][O:13][N:14]1[CH:15]([CH3:16])[CH2:3][C:2]([CH3:1])=[CH:4][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:11]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 535486Acetaldehyde, O-methyloximeHCID 714262142-(Prop-1-en-2-yl)cycloheptanone

Product 1

HCID 131735805(E)-1-methoxy-9,11-dimethylazacycloundec-8-en-2-oneYield 90%

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-methyl oxime (0.56 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 (1.29 g, 90% yield).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c5123d77941e4b1bae63926ebdd05f9a
Source dataset
uspto-grants-2016_06
Patent number
US09371262B2

Reaction notes

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