Iodoethane → HCID 58841176, compound

HRID 1269351Notes

Reaction equation

HRID 1269351 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([O:9][CH2:10]/[C:11](/[C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1)=[C:12](/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)\[C:13]([OH:15])=[O:14])=[O:8].[CH2:32](I)[CH3:33].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([O:9][CH2:10]/[C:11](/[C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:24][CH:23]=1)=[C:12](/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)\[C:13]([O:15][CH2:32][CH3:33])=[O:14])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 18448167HCID 18448167, compound

Product 1

HCID 58841176HCID 58841176, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5 mmol of (2Z)-4-{[(4-bromobutoxy)carbonyl]oxy}-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid with 3 mL of EtI in 30 mL of DMF was stirred with 5 mmol of K2CO3 at rt for 30 min. The reaction was quenched with sat. NH4Cl/H2O, extracted with EtOAc, Dried over Na2SO4, evaporated, and purified by flash chromatography (5–50% EtOAc/hexane) to afford 2.7 g of the titled compound. 1H NMR (acetone-d6, 500 MHz): δ 7.80 (d, 2 H), 7.48 (d, 2 H), 7.22–7.17 (m, 3 H), 7.15–7.08 (m, 2 H), 5.30 (s, 2 H), 4.32 (m, 4 H), 3.54 (t, 2 H), 3.12 (s, 3 H), 1.95–1.84 (m, 2 H), 1.83–1.70 (m, 2 H) 1.31 (t, 3 H).

Workup

  1. customThe reaction was quenched with sat. NH4Cl/H2O
  2. extractionextracted with EtOAc
  3. dry with materialDried over Na2SO4
  4. customevaporated
  5. custompurified by flash chromatography (5–50% EtOAc/hexane)

Sources & evidence

ORD record
ord-f4f1fe244e264e5f958d8c059dc5090a
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

Loading…