Sodium borohydride → 1-Hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 344047Notes

Reaction equation

HRID 344047 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:30]([O:32][CH2:33][CH3:34])=[O:31])[C:24]2=[O:29])([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.[BH4-].[Na+]>C(O)C.O1CCCC1>[OH:29][CH:24]1[C:25]2[C:20](=[C:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH:23]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 540112435-t-Butyldiphenylsilyloxy-2-ethoxycarbonyl-1-oxo-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 536494731-Hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthaleneYield 46.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-t-butyldiphenylsilyloxy-2-ethoxycarbonyl-1-oxo-1,2,3,4-tetrahydronaphthalene (17 g) in a mixture of ethanol (100 ml) and tetrahydrofuran (100 ml) was added NaBH4 (1.4 g) at 0° C. After the mixture was stirred for 6 hours at room temperature, the solvent was removed in vacuo. The residue was dissolved in a mixture of ethyl acetate and water and the organic solution was washed with 1N-HCl solution, sat. NaHCO3, and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-hydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (7.9 g).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. washthe organic solution was washed with 1N-HCl solution, sat. NaHCO3, and brine
  4. customThe dried solvent was evaporated in vacuo
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2d97f6d9e7454884a9d81573505e6139
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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