Sodium Carbonate → HCID 53940446, compound

HRID 344053Notes

Reaction equation

HRID 344053 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][CH:23]=[C:24]2[CH2:29][CH2:30][OH:31])([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.C([O-])([O-])=[O:33].[Na+].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C@H:23]([OH:33])[C@@H:24]2[CH2:29][CH2:30][OH:31])([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

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 54222647HCID 54222647, compound

Product 1

HCID 53940446HCID 53940446, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-t-butyldiphenylsilyloxy-1-(2-hydroxyethyl)-3,4-dihydronaphthalene (1.0 g) in CH2Cl2 (30 ml) were added Na2CO3 (290 mg) and m-chloroperbenzoic acid (750 mg) at 0° C. After being stirred for 2 hours, the solvent was removed in vacuo. The residue was extracted with ethyl acetate. The mixture was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was dissolved into tetrahydrofuran (20 ml) and LiAlH4 (200 mg) was added at 0° C. After being stirred for 2 hours, the reaction was quenched by saturated potassium sodium tartrate solution. After filtration, the solvent was removed, and the residue was purified by chromatography on silica gel to afford (cis)-5-t-butyldiphenylsilyloxy-1-(2-hydroxyethyl)-2-hydroxy-1,2,3,4-tetrahydronaphthalene (1.1 g).

Workup

  1. customthe solvent was removed in vacuo
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe mixture was washed with 1N-HCl solution, sat. NaHCO3, and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved into tetrahydrofuran (20 ml) and LiAlH4 (200 mg)
  7. additionwas added at 0° C
  8. stirringAfter being stirred for 2 hours
  9. customthe reaction was quenched by saturated potassium sodium tartrate solution
  10. filtrationAfter filtration
  11. customthe solvent was removed
  12. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4e6836edb5c345989440e6d8bf894cfc
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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