Oxygen → tert-Butyl (9-benzyl-1-methylthiocarbazol-2-yl)hydroxyacetate

HRID 1417460Notes

Reaction equation

HRID 1417460 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:11]([N:18]1[C:30]2[C:29]([S:31][CH3:32])=[C:28]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O:41]=O.[Cl-].[NH4+]>O1CCCC1>[CH2:11]([N:18]1[C:30]2[C:29]([S:31][CH3:32])=[C:28]([CH:33]([OH:41])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 977OxygenHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 53762851Tert-butyl (9-benzyl-1-methylthiocarbazol-2-yl)acetate

Product 1

HCID 54448718tert-Butyl (9-benzyl-1-methylthiocarbazol-2-yl)hydroxyacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.47 ml of a 1.0M solution of lithium hexamethyldisilazide in tetrahydrofuran was added, with ice-cooling, to a solution of 65 mg of tert-butyl (9-benzyl-1-methylthiocarbazol-2-yl)acetate, as obtained in Example 4, in 5 ml of tetrahydrofuran. The reaction mixture was then stirred for 1 hour in the presence of atmospheric oxygen. After this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. The aqueous layer was extracted with ethyl acetate and the organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 1.5 g of silica gel with a 3:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 43 mg of the title compound as an oil.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. extractionthe organic extract
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. additionwith a 3:1 v/v mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-7217921a05514dc9a5e5fb14d4e2cc85
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

Loading…