Ammonium Chloride → Ethyl 6-(2,6-dimethoxyphenyl)-6-(1,1-dimethylethylsulfinamido)hexanoate

HRID 594333Notes

Reaction equation

HRID 594333 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[Li]CCCC.[C:17]([S:21]([N:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:22])([CH3:20])([CH3:19])[CH3:18].[NH4+].[Cl-]>C1COCC1.O.CCOCC>[CH3:11][O:10][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[CH:24]([NH:23][S:21]([C:17]([CH3:18])([CH3:20])[CH3:19])=[O:22])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 113914072-Iodo-1,3-dimethoxybenzeneHCID 86695621Ethyl 6-((tert-butylsulfinyl)imino)hexanoateHCID 178418339Butyllithium

Product 1

HCID 69082536Ethyl 6-(2,6-dimethoxyphenyl)-6-(1,1-dimethylethylsulfinamido)hexanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A cooled (−78° C.) yellow solution of 2-iodo-1,3-dimethoxybenzene (6.337 g; 24.00 mmol) in anh. THF (130 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (15.0 ml; 24.00 mmol). The resulting yellow solution was further stirred at −78° C. for 15 min. A yellow solution of ethyl 6-((tert-butylsulfinyl)imino)hexanoate (5.018 g; 19.20 mmol) in anh. THF (12 ml) was then added dropwise to the cooled reaction mixture, and stirring at −78° C. was continued for 50 min. The resulting orange reaction mixture was treated successively with aq. sat. NH4Cl (65 ml), Et2O (200 ml) and water (60 ml). The separated yellow organic layer was then washed with brine (60 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded ethyl 6-(2,6-dimethoxyphenyl)-6-(1,1-dimethylethylsulfinamido)hexanoate as a yellow oil. LC-MS (conditions B): tR=0.91 min.; [M+H]+: 400.05 g/mol.

Workup

  1. stirringstirring at −78° C.
  2. waitwas continued for 50 min
  3. washThe separated yellow organic layer was then washed with brine (60 ml)
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=25/1)

Sources & evidence

ORD record
ord-4029a35260d6461381411e982712d388
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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