Ethyl bromoacetate → Ethyl [(4,4-dimethyl-3,4-dihydro-2H-chromen-7-yl)oxy]acetate

HRID 1350878Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 11430Potassium Carbonate

HCID 157297964,4-dimethyl-3,4-dihydro-2H-1-benzopyran-7-ol

Product 1

HCID 58640424Ethyl [(4,4-dimethyl-3,4-dihydro-2H-chromen-7-yl)oxy]acetateYield 99.3%

Procedure

4,4-Dimethylchroman-7-ol (1.4 g, 8.0 mmol), potassium carbonate (3.3 g, 24.0 mmol) and ethyl bromoacetate (1.0 mL, 9.2 mmol) were treated in the same procedure described in Example 33(d). 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 4/1) to furnish 2.1 g (98% yield) of the title compound as a colorless oil.

Workup

washeluted with a volume mixture of hexane and ethyl acetate (19/1 to 4/1)

Sources & evidence

ORD record: ord-2d9d3be759c444f2850e18cba3ce4b3c
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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