Bis(2-chloroethyl) ether → HCID 22033316, compound

HRID 1792297Notes

Reaction equation

[OH:1][C:2]1([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][O:14][CH3:15])=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:18][CH:17]=1.[Cl:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38]Cl.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O.O>[OH:1][C:2]1([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:38][CH2:37][O:36][CH2:35][CH2:34][Cl:33])=[CH:30][CH:31]=2)[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][O:14][CH3:15])=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Hydroxy-4-(4-hydroxyphenyl)-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman (770 mg, 1.4 mmol), bis-(2-chloroethyl)ether (810 mg, 5.7 mmol), potassium carbonate (782 mg, 5.7 mmol) and 18-crown-6(132 mg, 0.49 mmol) were dissolved in dry N,N-dimethylformamide (10 mL) under argon atmosphere, which was then stirred at 100° C. for 2.5 hours. The reaction solution was cooled down to normal temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to flash column chromatography (n-hexane:ethyl acetate=2:1) to give the title compound (0.71 g, yield 35%) as a red oil.

Workup

additionwas added
extractionthe mixture was extracted with ethyl acetate
extractionThe organic extract
dry with materialwas dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-88524f79356d4db1b390048dfdf898d3
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074819B2

Reaction notes

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