Diisopropylamine → HCID 21895492, compound

HRID 2118284Notes

Reaction equation

HRID 2118284 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.C(NC(C)C)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[CH3:20][S:21]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 31297Methanesulfonyl chlorideHCID 21895421HCID 21895421, compound

Product 1

HCID 21895492HCID 21895492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Iodophenyl)butan-1-ol (1.7 g) was stirred with diisopropylamine (1.74 ml) and methanesulfonyl chloride (0.66 ml) in dichloromethane (50 ml) at 21° for 2 h. The solution was washed successively with sodium bicarbonate solution, water, water acidified with a few drops of 2M HCl and water, each time back extracting with dichloromethane. The combined organic layers were dried (MgSO4) and evaporated to give the title compound (2.23 g), tlc Rf=0.28 (1:3 ethyl acetate in cyclohexane)

Workup

  1. washThe solution was washed successively with sodium bicarbonate solution, water, water
  2. extractioneach time back extracting with dichloromethane
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-208c3f74f2244a768aa58ab765bfe296
Source dataset
uspto-grants-2008_10
Patent number
US07442837B2

Reaction notes

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