Ethyl bromoacetate → Ethyl [4-tert-butyl-3-(cyclopropylmethoxy)phenoxy]acetate

HRID 1350868Notes

Reaction equation

HRID 1350868 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[O:12][CH2:13][CH:14]1[CH2:16][CH2:15]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]=1[O:12][CH2:13][CH:14]1[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 210974984-tert-Butyl-3-(cyclopropylmethoxy)phenol

Product 1

HCID 58640408Ethyl [4-tert-butyl-3-(cyclopropylmethoxy)phenoxy]acetateYield 75.6%

Procedure

4-tert-Butyl-3-(cyclopropylmethoxy)phenol (444 mg, 2.0 mmol), sodium hydride (60% in mineral oil) (68 mg, 1.7 mmol) and ethyl bromoacetate (270 II, 2.4 mmol) were treated in the same procedure described in Example 31(c). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1) to furnish 463 mg (75% yield) of the title compound as a yellow oil.

Workup

  1. washeluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1)

Sources & evidence

ORD record
ord-4ef7b2ce86d7458dabb51b697b335271
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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