Water → HCID 86591228, compound

HRID 1372183Notes

Reaction equation

HRID 1372183 reaction equation
[I:1]N1C(=O)CCC1=O.[O:9]1[CH:13]=[CH:12][CH2:11][CH2:10]1.[CH2:14]([OH:17])[C:15]#[CH:16].O>C(Cl)Cl>[CH2:14]([O:17][C@H:13]1[C@H:12]([I:1])[CH2:11][CH2:10][O:9]1)[C:15]#[CH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 709342,3-DihydrofuranHCID 120273N-Iodosuccinimide

Product 1

HCID 86591228HCID 86591228, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
24 °C

Procedure

To a stirred, ice cold suspension of 15 g (66.6 mmol) of N-iodosuccinimide in 150 mL of CH2Cl2 was added a mixture of dihydrofuran (66.6 mmol, 4.67 g, 5.1 mL) and propargyl alcohol (100 mmol, 5.0 g, 5.2 mL) in 50 mL of CH2Cl2 over 20 min. After warming to 24° C. with stirring over 2 hours, 200 mL of water was added and the stirring was continued for 1 hour. The layers were separated and the aqueous layer extracted with 2×100 mL of CH2Cl2. The combined organic extracts were washed with a brine solution containing a small amount of sodium thiosulfate (Na2S2O3) (70 mg), dried over anhydrous Na2SO4, filtered, and concentrated. Chromatography over silica gel using 30% EtOAc in hexane yielded (15.4 g, 92%) of iodoether 10 as an oil. 1H-NMR (CDCl3): δ 5.4 (br s, 1H), 4.0–4.3 (m, 5H), 2.7 (m, 1H), 2.48 (br s, 1H), 2.25 (m, 1H); IR (neat), 2956, 2180, 1621, 1440 cm−1.

Workup

  1. additionwas added
  2. waitthe stirring was continued for 1 hour
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with 2×100 mL of CH2Cl2
  5. washThe combined organic extracts were washed with a brine solution
  6. additioncontaining a small amount of sodium thiosulfate (Na2S2O3) (70 mg)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-86631e67624644cdab6f5f95cafa954e
Source dataset
uspto-grants-2007_01
Patent number
US07157489B2

Reaction notes

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