Dimethylformamide → HCID 85850169, compound

HRID 898204Notes

Reaction equation

HRID 898204 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1>[CH2:9]([S:8][C:5]1[CH:6]=[CH:7][C:2]([CH:26]=[O:27])=[CH:3][CH:4]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12521247HCID 12521247, compoundHCID 178418339Butyllithium

Product 1

HCID 85850169HCID 85850169, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3.15 g (10.0 mmol) of 1-bromo-4-(nonylthio)benzene in 50 mL anhydrous THF was slowly added 9.4 mL of n-BuLi (1.6 M in hexanes, 15 mmol) at −50° C. The mixture was aged at the same temperature for 1 h before the addition of 2.3 mL of anhydrous DMF. The reaction mixture was allowed to warm to 0° C. and was quenched with 2 N HCl to pH=1. The layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL×2). The combined organic layer and extractions were washed with water and concentrated to oil. Flash chromatography on a Biotage 40M cartridge using 5% ethyl acetate/hexanes afforded 2.35 g (89%) of the title compound as light yellow oil: 1H NMR (500 MHz) δ 0.91 (t, J=7.0, 3H), 1.30-1.76 (m, 14H), 3.03 (t, J=7.4, 2H), 7.37 (d, J=8.5, 2H), 7.78 (d, J=8.5, 2H), 9.95 (s, 1H); LC-1: 4.8 min; ESI-MS 265 (M+H).

Workup

  1. customat −50° C
  2. customwas quenched with 2 N HCl to pH=1
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (50 mL×2)
  5. extractionThe combined organic layer and extractions
  6. washwere washed with water
  7. concentrationconcentrated to oil

Sources & evidence

ORD record
ord-5e7dcce10a9a4e5e9566195e6e9ef7f7
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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