1,5-Pentanediol → HCID 18970864, compound

HRID 1078993Notes

Reaction equation

HRID 1078993 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[Si:10](Cl)([C:13](C)(C)C)([CH3:12])[CH3:11]>C1COCC1>[CH3:11][Si:10]([CH3:13])([CH3:12])[O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:7]

Participants

5

Reactant 3

HCID 81051,5-PentanediolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18970864HCID 18970864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,5-pentandiol (44 mmol) in THF (15 mL) is cooled to 0° C. and treated with sodium hydride (44 mmol) followed by tert-butyldimethylsilyl chloride (44 mmol). The reaction mixture is stirred at room temperature overnight. Concentration in vacuo and flash chromatography affords 5-trimethylsiloxy-1-pentanol. To a solution of 5-trimethylsiloxy-1-pentanol (11.6 mmol) in dry dichloromethane (50 mL) is added 2,6-di-tert-butyl-4methylpyridine (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-trimethylsiloxy-1-pentyl triflate (45) which is used without further purification.

Workup

  1. concentrationConcentration in vacuo and flash chromatography

Sources & evidence

ORD record
ord-d81d409644ca41d7b06452e5ad62e231
Source dataset
uspto-grants-1996_08
Patent number
US05550251

Reaction notes

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