Diisopropylamine → HCID 21895492, compound

HRID 720833Notes

Reaction equation

HRID 720833 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-af1ec83cef6442efa7842042885a92f8
Source dataset
uspto-grants-2006_11
Patent number
US07135600B2

Reaction notes

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