1,6-Hexanediol → HCID 18970836, compound

HRID 399323Notes

Reaction equation

HRID 399323 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[H-].[Na+].[Si:11](Cl)([C:14](C)(C)C)([CH3:13])[CH3:12]>C1COCC1>[CH3:12][Si:11]([CH3:14])([CH3:13])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:8]

Participants

5

Reactant 3

HCID 123741,6-HexanediolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18970836HCID 18970836, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,6-hexandiol (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 6-trimethylsiloxy-1-hexanol. To a solution of 6-trimethylsiloxy-1-hexanol (11.6 mmol) in dry dichloromethane (50 mL) is added 2,6-di-tert-butyl-4-methylpyridine (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 6-trimethylsiloxy-1-hexyl triflate (40) which is used without further purification.

Workup

  1. concentrationConcentration in vacuo and flash chromatography

Sources & evidence

ORD record
ord-1c3a2cf259f94c90ad0a6133a149d5d7
Source dataset
uspto-grants-1998_10
Patent number
US05817879

Reaction notes

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