Ethyl bromoacetate → HCID 53791634, compound

HRID 1682950Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:10]#N)[CH:5]=[CH:6][C:7]=1[Cl:8].[Li+].C[CH:23]([N-:25]C(C)C)C.BrC[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C1COCC1>[CH2:34]([O:33][C:31](=[O:32])[CH:10]([C:23]#[N:25])[CH:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:12][CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[CH3:35]

Participants

Conditions

Temperature: 20 °C

Procedure

2-(3,4-dichloro-phenyl)-4-(tetrahydro-pyran-2yloxy)-butyronitrile (10.8669 g, 34.62 mmol) was dissolved in THF (20 mL) at -78° C. and treated dropwise with LDA (27.2 mL, 40.8 mmol, 1.18 eq.) over 30 minutes. The solution was allowed to stir for 1.25 hour. Ethyl bromoacetate (4.2 mL, 37.87 mmol, 1.09 eq.) was added dropwise at -78° C. and the solution was allowed to warm to 20° C. and stir for 4 hours. The solution was partitioned between ammonium chloride and diethyl ether. The organic solution was extracted with water and brine and the organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (400 g) with a gradient from 20% ethyl acetate in hexane to 30% ethyl acetate in hexane to give 9.6243 g (69.5%) of the title compound.

Workup

stirringstir for 4 hours
customThe solution was partitioned between ammonium chloride and diethyl ether
extractionThe organic solution was extracted with water and brine
dry with materialthe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel (400 g) with a gradient from 20% ethyl acetate in hexane to 30% ethyl acetate in hexane

Sources & evidence

ORD record: ord-11c68690da154fff888f6f3b64724a5f
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05635510

Reaction notes

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