Ethyl bromoacetate → HCID 21293350, compound

HRID 622073Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[C:9]3=[CH:11][C:12](=[O:15])[CH2:13][CH2:14][C:8]3([CH2:16][CH2:17][CH3:18])[O:7][C:6]=2[CH:5]=[C:4](O)[C:3]=1[Cl:20].Br[CH2:22][C:23]([O:25]CC)=[O:24]>CN(C)C=O>[Cl:1][C:2]1[C:10]2[C:9]3=[CH:11][C:12](=[O:15])[CH2:13][CH2:14][C:8]3([CH2:16][CH2:17][CH3:18])[O:7][C:6]=2[CH:5]=[C:4]([CH2:22][C:23]([OH:25])=[O:24])[C:3]=1[Cl:20]

Participants

Conditions

Temperature: 65 °C

Procedure

A stirred mixture of 1,2-dichloro-3-hydroxy-8-oxo-5a-propyl-5a,6,7,8-tetrahydrodibenzofuran (0.4 g) potassium carbonate (0.2 g) and ethyl bromoacetate (200 μl) in N,N-dimethylformamide (7 ml) was heated at 65° C. for 1 1/4 hours. The reaction mixture was poured into ice water and the solid ester which precipitated was removed by filtration then dissolved in methanol (15 ml) containing water (1 ml) and 10N sodium hydroxide (1 ml). After 1/2 hour the methanol solution was poured into dilute aqueous hydrochloric acid, extracted with ether which was washed with water, brine, dried over MgSO4 and evaporated in vacuo. Trituration of the residue with methylene chloride gave 0.35 g of (1,2-dichloro-8-oxo-5a-propyl-5a,6,7,8-tetrahydrodibenzofuran-3-yl)acetic acid which melted at 248°-250° C.

Workup

customthe solid ester which precipitated
customwas removed by filtration
dissolutionthen dissolved in methanol (15 ml)
additioncontaining water (1 ml) and 10N sodium hydroxide (1 ml)
additionAfter 1/2 hour the methanol solution was poured into dilute aqueous hydrochloric acid
extractionextracted with ether which
washwas washed with water, brine
dry with materialdried over MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-b332dd28ad734f68bc95c0541663a570
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04769370

Reaction notes

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