Water → HCID 59299392, compound

HRID 2235195Notes

Reaction equation

HRID 2235195 reaction equation
C[Si](C)(C)[N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[Li+].CC([N-]C(C)C)C.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH2:27]Cl.O>C1COCC1>[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH2:27][CH:5]1[CH2:6][CH2:7][NH:3][C:4]1=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 844611-(Trimethylsilyl)pyrrolidin-2-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 59299392HCID 59299392, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Charge a flask with 1-trimethylsilanyl-pyrrolidin-2-one (5.0 g, 32 mmol), dissolve in THF (150 mL) and cool to −78° C. under nitrogen. Add LDA (2M, 19 mL, 38 mmol) and stir at −78° C. for 10 minutes. Add 2,4-dichloro-1-chloromethyl-benzene (8.1 g, 41 mmol) and warm to room temperature. Pour into water after 2 hours and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify the residue over silica gel (1:1 hexanes:ethylacetate to 100% ethyl acetate) to afford 5.2 g (67%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.38 (d, 1H), 7.23 (d, 1H), 7.18 (dd, 1H), 6.01 (bs, 1H), 3.31 (m, 3H), 2.75 (m, 2H), 2.13 (m, 1H), 1.84 (m, 1H).

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue over silica gel (1:1 hexanes:ethylacetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-acd8336eeae645d0ab29398c9fca942d
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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