Water → HCID 70188016, compound

HRID 344056Notes

Reaction equation

HRID 344056 reaction equation
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C:23](=[O:47])[CH:24]2[CH2:29][CH2:30][O:31][C:32](=[O:46])[N:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:48][Mg]Br.C(OCC)(=O)C.O>O1CCCC1>[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C:23]([OH:47])([CH3:48])[CH:24]2[CH2:29][CH2:30][O:31][C:32](=[O:46])[N:33]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23224043HCID 23224043, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 70188016HCID 70188016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-t-butyldiphenylsilyloxy-1-[2-(N,N-diphenylcarbamoyloxy)ethyl]-2-oxo-1,2,3,4-tetrahydronaphthalene (0.9 g) in THF (tetrahydrofuran) (20 ml) was added methylmagnesium bromide (2.0 ml, 1M solution in THF) at 0° C. under N2. After being stirred for 1 hour at the room temperature, the solution was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 5-t-butyldiphenylsilyloxy-1-[2-(N,N-diphenylcarbamoyloxy)ethyl]-2-hydroxy-2-methyl-1,2,3,4-tetrahydronaphthalene (0.6 g).

Workup

  1. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3059182eded040dcb8d780cb56b36356
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

Loading…