Tetrahydrofuran → HCID 53859638, compound

HRID 1086378Notes

Reaction equation

HRID 1086378 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2OCC(C)(C)N=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([Li])(CC)C.C(=O)=[O:26].[C:28](#[N:30])C.CS[S:33][CH3:34].[NH4+].[Cl-].C1C[O:40][CH2:39][CH2:38]1>>[CH3:34][S:33][C:10]1[CH:11]=[CH:12][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][C:9]=1[CH:13]=[CH:38][C:39]([N:30]([OH:26])[CH3:28])=[O:40]

Participants

7

Reactant 6

HCID 8028Tetrahydrofuran2×HCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 19827203HCID 19827203, compoundHCID 86587134Acetonitrile dry iceHCID 178418400CID 53628100

Product 1

HCID 53859638HCID 53859638, compound

Procedure

To a solution of 2-(3-n-hexylphenyl)-4,4-dimethyl-oxazoline (21 g, 0.086 mmol) in 200 ml of dry THF is added dropwise, sec-butyllithium (73 ml) at a temperature of -40° C. (dry ice/acetonitrile bath). After stirring one hour at -40° C. a solution of dimethyldisulfide (8.18 g, 0.087 mmol) in THF (7.82 ml) is then added dropwise to the reaction mixture and stirred for 2 hours while keeping the temperature at -40° C. The reaction mixture is poured into saturated NH4Cl and then extracted with ethyl acetate. The extracts are washed with water and then brine, dried over MgSO4 and concentrated to afford the subtitle compound.

Workup

  1. additionis then added dropwise to the reaction mixture
  2. customat -40° C
  3. extractionextracted with ethyl acetate
  4. washThe extracts are washed with water
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2b34307217df4f96b238124e9db30119
Source dataset
uspto-grants-1991_07
Patent number
US05028629

Reaction notes

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