Tin tetrachloride → (E)-1-methoxy-8-methyl-10-pentyl-3,4,5,6,9,10-hexahydroazecin-2(1H)-one

HRID 2205255Notes

Reaction equation

HRID 2205255 reaction equation
[CH2:1]=[C:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])[CH3:3].[CH2:11]([O:13][N:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])C.Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH3:11][O:13][N:14]1[CH:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][C:2]([CH3:1])=[CH:4][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 11018939Cyclohexanone, 2-(1-methylethenyl)-HCID 53992913HCID 53992913, compound

Product 1

HCID 131735803(E)-1-methoxy-8-methyl-10-pentyl-3,4,5,6,9,10-hexahydroazecin-2(1H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Following the general procedure as described in Example 17, 2-(prop-1-en-2-yl)cyclohexanone (0.88 g, 6.38 mmol), hexanal O-ethyl oxime (0.99 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 (1.00 g, 59% yield). E isomer>98%.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4cf36810dec34a169919c08b278a0534
Source dataset
uspto-grants-2016_06
Patent number
US09371262B2

Reaction notes

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