Isopropyl iodide → Ethyl {3-methoxy-4-[(propan-2-yl)oxy]phenyl}acetate

HRID 535307Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[CH:5](CC)[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].I[CH:25]([CH3:27])[CH3:26]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:25]([CH3:27])[CH3:26])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl (4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester (11.22 g, 53.4 mmol) and K2CO3 (22.13 g, 160 mmol) in DMF (100 ml) was heated at 60° C. 2-Iodopropane (9.06 ml, 91 mmol) was added and the mixture was vigorously stirred at 60° C. for 5 h. The reaction mixture was cooled to RT, diluted with AcOEt and washed with water. The aqueous phase was separated and further extracted with AcOEt. The combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/AcOEt 98:2→3:1) to yield the title compound (11.94 g, 47.3 mmol, 89%) as a colorless oil.

Workup

temperatureThe reaction mixture was cooled to RT
washwashed with water
customThe aqueous phase was separated
extractionfurther extracted with AcOEt
dry with materialThe combined organic fractions were dried over Na2SO4
filtrationfiltered
customevaporated to dryness
customThe resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/AcOEt 98:2→3:1)

Sources & evidence

ORD record: ord-5f39af998b444e449f66f1b6649610e8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859535B2

Reaction notes

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