Sodium hydride → trans-3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-1-(4-carbomethoxymethyl-2-bromophenoxy)cyclohexane

HRID 2413952Notes

Reaction equation

HRID 2413952 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([O:15]S(C)(=O)=O)[CH2:10]2)=[C:6]([CH2:22][CH2:23][CH3:24])[C:5]=1[OH:25])(=[O:3])[CH3:2].O[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:29][C:28]=1[Br:38].[H-].[Na+].C1OCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.C1COCC1>[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([O:15][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:29][C:28]=3[Br:38])[CH2:10]2)=[C:6]([CH2:22][CH2:23][CH3:24])[C:5]=1[OH:25])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 10634081Methyl 2-(3-bromo-4-hydroxyphenyl)acetateHCID 88643326HCID 88643326, compound

Product 1

HCID 70410445trans-3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-1-(4-carbomethoxymethyl-2-bromophenoxy)cyclohexane

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound of Step C of this example (500 mg; 1.35 mmole) in toluene (30 ml) and THF (1.5 ml) was added successively 4-hydroxy-3-bromophenylacetic acid, methyl ester (1 g, 4 mmoles), sodium hydride (169 mg; 7 mmoles) and 15-crown-5 (10 mg). The reaction mixture was refluxed for 10 hours under nitrogen. It was then worked-up as in Step B of Example 8 to yield the title compound of this step.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 hours under nitrogen

Sources & evidence

ORD record
ord-9c51314325954289be535469f13caeb8
Source dataset
uspto-grants-1988_01
Patent number
US04720505

Reaction notes

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