Sodium Hydroxide → HCID 19820412, compound

HRID 1030469Notes

Reaction equation

[Cl-].[Cl-].[Cl-].[Al+3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:35]=[CH:34][C:15]2[O:16][C:17]3[CH:33]=[CH:32][CH:31]=[CH:30][C:18]=3[CH2:19][CH2:20][N:21]([C:25](OCC)=O)[CH2:22][CH2:23][O:24][C:14]=2[CH:13]=1.[OH-].[Na+]>C(OCC)C.O1CCCC1>[Cl:11][C:12]1[CH:35]=[CH:34][C:15]2[O:16][C:17]3[CH:33]=[CH:32][CH:31]=[CH:30][C:18]=3[CH2:19][CH2:20][N:21]([CH3:25])[CH2:22][CH2:23][O:24][C:14]=2[CH:13]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A suspension of 3.13 g of aluminum trichloride in 110 ml of diethyl ether was added to a suspension of 1.56 g lithium aluminum hydride in 110 ml of diethyl ether and then cooled to approx. 5° C., after which a solution of 4.27 g of ethyl 3-chloro-7,8,9,10-tetrahydro-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine-8-carboxylate 92 ml of tetrahydrofuran was slowly added. After 1 h the aluminum complex was decomposed by addition of 21 ml of 1N sodium hydroxide solution. After 30 min stirring the salts were removed with suction and rinsed with dichloromethane. After evaporation of the solvent 3.6 g of crude product was obtained, which was purified by silica chromatography with toluene-ethanol (9:1) to obtain pure 3-chloro-7,8,9,10-tetrahydro-8-methyl-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine. After conversion into the maleate and recrystallization from ethanol-diethylether 2.6 g (52%) of 3-chloro-7,8,9,10-tetrahydro-8-methyl-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine (Z)-2-butenedioate (1:1), mp 145°-157° C., was obtained.

Workup

customwere removed with suction
washrinsed with dichloromethane
customAfter evaporation of the solvent 3.6 g of crude product
customwas obtained
customwhich was purified by silica chromatography with toluene-ethanol (9:1)

Sources & evidence

ORD record: ord-916cf83f3ede4951964b80314b21ac05
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05106839

Reaction notes

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