Tetrahydrofuran → {2-[2-(4-Chlorobutoxy)-ethoxy]ethyl}-carbamic acid anthracen-9-ylmethyl ester

HRID 1919262Notes

Reaction equation

HRID 1919262 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][O:16][C:17](=[O:25])[NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1COCC1.[Cl:33][CH2:34][CH2:35][CH2:36][CH2:37]I>CCCCCCC.C(OCC)(=O)C>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][O:16][C:17](=[O:25])[NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:37][CH2:36][CH2:35][CH2:34][Cl:33])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 825271-Chloro-4-iodobutaneHCID 10315131[2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid anthracen-9-ylmethyl ester

Product 1

HCID 10025685{2-[2-(4-Chlorobutoxy)-ethoxy]ethyl}-carbamic acid anthracen-9-ylmethyl esterYield 32%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

A 50 ml round bottom flask was charged with [2-(2-Hydroxyethoxy)-ethyl]-carbamic acid anthracen-9-ylmethyl ester (0.25 g, 0.74 mmol) and fresh sodium hydride, 60% dispersion in mineral oil (150 mg, 3.75 mmol) under inert atmosphere. 10 ml anhydrous THF was added and the reaction allowed to stir for 5 minutes. After this point, 1-chloro-4-Iodobutane (180 μl, 1.5 mmol) is added via syringe. The reaction is stirred at room temperature for 24 hours. Silica gel 60 is co-absorbed onto the reaction mixture with loss of solvent under reduced pressure. Silica gel column chromatography takes place initially with heptane as eluent, followed by 10%, 20%, and 30% ethyl acetate. A total of 0.1 g (32% yield) of product is isolated from appropriate fractions:

Workup

  1. stirringThe reaction is stirred at room temperature for 24 hours

Sources & evidence

ORD record
ord-d61de50e4a294e7d83b8ff92ed435bef
Source dataset
uspto-grants-2012_05
Patent number
US08168405B2

Reaction notes

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