Diethyl Ether → HCID 22164620, compound

HRID 1032630Notes

Reaction equation

HRID 1032630 reaction equation
[H-].[Na+].[CH:3]1([OH:14])[CH:12]2[CH:7]([CH:8]([OH:13])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5][CH2:4]1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(OCC)C>O1CCCC1>[Si:15]([O:14][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]2[CH:12]1[CH2:11][CH2:10][CH2:9][CH:8]2[OH:13])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 103728Decahydronaphthalene-1,5-diol

Product 1

HCID 22164620HCID 22164620, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
56 °C

Procedure

A suspension of 0.45 gm (12 mmole) of sodium hydride dispersion (60%) in 75 mL of tetrahydrofuran was treated with 2.0 gm (12 mmole) of 1,5-decalindiol in an inert atmosphere. This mixture was stirred overnight at about 56° C. then cooled to room temperature and 1.8 gm (12 mmole) of t-butyldimethylsilyl chloride added. The mixture was stirred at room temperature for 4 days then 200 mL of diethyl ether added followed by washing the resulting mixture with 10% aqueous potassium carbonate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was subjected to flash chromatography on 40 microns silica gel to give 5-(t-butyldimethylsilyloxy)-1 -hydroxydecalin as a clear, colorless oil. Satisfactory ir, cmr and pmr spectra were obtained.

Workup

  1. temperaturethen cooled to room temperature
  2. stirringThe mixture was stirred at room temperature for 4 days
  3. washby washing the resulting mixture with 10% aqueous potassium carbonate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f149dd19bd24a42ba33d44743096cdc
Source dataset
uspto-grants-1990_09
Patent number
US04959293

Reaction notes

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