tert-Butyldimethylsilyl chloride → HCID 86672802, compound

HRID 1755130Notes

Reaction equation

HRID 1755130 reaction equation
[F:1][C:2]([F:13])([C:5]([F:12])([F:11])[C:6]([F:10])([F:9])[CH2:7][OH:8])[CH2:3][OH:4].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:17]([Si:14]([CH3:16])([CH3:15])[O:8][CH2:7][C:6]([F:10])([F:9])[C:5]([F:11])([F:12])[C:2]([F:13])([F:1])[CH2:3][OH:4])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67831Hexafluoroamylene glycol

Product 1

HCID 86672802HCID 86672802, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (634 mg, 5.2 mmol) was added to a solution of 2,2,3,3,4,4-hexafluoro-pentane-1,5-diol (1 g, 4.7 mmol) and tert-butyldimethylsilyl chloride (708 mg, 4.7 mmol) in methylene chloride (10 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography to give 5-(tert-butyl-dimethyl-silanyloxy)-2,2,3,3,4,4-hexafluoro-pentan-1-ol (770 mg, 50%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bcc690aab41a4cf6bcc6e7779231f5bf
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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