Ethyl bromoacetate → Ethyl (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetate

HRID 1834680Notes

Reaction equation

[CH2:1]([CH:3]1[CH2:11][C:10]2[C:5](=[C:6]([Cl:14])[C:7]([Cl:13])=[C:8]([OH:12])[CH:9]=2)[C:4]1=[O:15])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O>[O:15]=[C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:12][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:7]([Cl:13])[C:6]=2[Cl:14])[CH2:11][CH:3]1[CH2:1][CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-ethyl-5-hydroxy-6,7-dichloro-1-indanone (9.8 g., 0.04 mole), dimethylformamide (30 ml.), potassium carbonate (12.5 g., 0.09 mole) and ethyl bromoacetate (15 g., 0.09 mole) is stirred and heated on a water bath at 60° C. for one hour. The reaction mixture is poured into ice water (200 ml.) and extracted with two 50 ml. portions of ether. The ether extract is washed with water, dried over magnesium sulfate and the ether distilled at reduced pressure. The ethyl (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetate thus obtained melts at 116°-118° C. after recrystallization from ethyl alcohol.

Workup

extractionextracted with two 50 ml
extractionThe ether extract
washis washed with water
dry with materialdried over magnesium sulfate
distillationthe ether distilled at reduced pressure
customThe ethyl (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetate thus obtained melts at 116°-118° C. after recrystallization from ethyl alcohol

Sources & evidence

ORD record: ord-de51f3168d194251b2214bc579280f51
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04070539

Reaction notes

Loading…