1,5-Dibromopentane → HCID 54369773, compound

HRID 1648092Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:10]=1)[CH3:2].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][Br:24])=[C:11]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: 92 °C

Procedure

A mixture of 0.655 g (2.03 mmol) of 3-(3-ethoxy-3-oxopropyl)-4-hydroxybenzenepentanoic acid ethyl ester from the preceding example, 2.80 g (12.2 mmol) of 1,5-dibromopentane, 1.12 g (8.12 mmol) of anhydrous granular potassium carbonate, and 35 mL of 2-butanone was stirred at 92° C. for 22 hr. After being cooled to room temperature, the mixture was filtered through anhydrous magnesium sulfate and the solids were washed thoroughly with ethyl acetate and ether. The filtrate and washes were combined and concentrated in vacuo and the crude product was purified by flash chromatography on 80 g of silica gel, eluting with hexane-ethyl acetate (4:1). There was obtained 0.804 g (83.9%) of the title compound as a colorless oil.

Workup

temperatureAfter being cooled to room temperature
filtrationthe mixture was filtered through anhydrous magnesium sulfate
washthe solids were washed thoroughly with ethyl acetate and ether
concentrationconcentrated in vacuo
customthe crude product was purified by flash chromatography on 80 g of silica gel
washeluting with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record: ord-857a4e565e21435c8ad9abcdb27ca370
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05434186

Reaction notes

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