(Diethylamino)sulfur trifluoride → HCID 59305303, compound

HRID 2240931Notes

Reaction equation

HRID 2240931 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH2:9][CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][CH:7]=1.CCN(S(F)(F)[F:20])CC>C(Cl)Cl>[F:20][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)[CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59305345HCID 59305345, compound

Product 1

HCID 59305303HCID 59305303, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-Iodo-phenyl)-pent-4-en-1-ol (0.51 g, 1.77 mmol), in dry methylene chloride (10 mL) at −78° C. and under a nitrogen atmosphere was added DAST (0.28 mL, 2.1 mmol). The cooling bath was removed and the mixture was warmed to room temperature for 1 h, and then quenched with sat sodium bicarbonate (4 mL). The mixture was partitioned between methylene chloride and H2O, and the aqueous layer was extracted with methylene chloride (2×10 mL). The organic layer was washed with brine and dried over MgSO4, filtered and concentrated in vacuo to a clear oil (0.46 g, 90%) and used directly in the next step.

Workup

  1. customThe cooling bath was removed
  2. customquenched with sat sodium bicarbonate (4 mL)
  3. customThe mixture was partitioned between methylene chloride and H2O
  4. extractionthe aqueous layer was extracted with methylene chloride (2×10 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a clear oil (0.46 g, 90%)

Sources & evidence

ORD record
ord-f6c9b0bd32dd4b4b9a4f8881fd9502f1
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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