Hydrogen Peroxide → HCID 70187793, compound

HRID 344057Notes

Reaction equation

HRID 344057 reaction equation
[C:1]1([N:7]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:8]([O:10][CH2:11][CH2:12][C:13]2[C:22]3[C:17](=[C:18]([O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH:14]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].OO.C(OCC)(=[O:53])C>O1CCCC1.O>[C:41]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([O:10][CH2:11][CH2:12][C@@H:13]2[C:22]3[C:17](=[C:18]([O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][C@H:14]2[OH:53])=[O:9])[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 70186200HCID 70186200, compound

Product 1

HCID 70187793HCID 70187793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[2-(N,N-diphenylcarbamoyloxy)-ethyl]-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthalene (2.0 g) in THF (tetrahydrofuran) (20 ml) was added BH3 (4.8 ml, 1M solution in THF) at 0° C. under N2. After being stirred for 12 hours at the room temperature, 2N-NaOH solution (1.5 ml) and H2O2 (1.0 ml, 35% solution) were added to the solution and stirred for 4 hours. The mixture 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 (trans)-1-[2-(N,N-diphenylcarbamoyl-oxy)ethyl]-2-hydroxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.1 g).

Workup

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

Sources & evidence

ORD record
ord-4cdf4dbf066c44a4aebd311cbec7219c
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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