Dimethylformamide → HCID 21527996, compound

HRID 1658567Notes

Reaction equation

HRID 1658567 reaction equation
[OH:1][CH:2]([CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([CH3:11])([CH3:10])[C:4]#[C:5][Si](C)(C)C.[F-].[K+].CN(C)C=O>CCOCC.O>[CH3:11][C:3]([CH3:10])([CH:2]([OH:1])[CH2:12][CH2:13][CH2:14][CH3:15])[C:4]#[CH:5]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 21527997HCID 21527997, compound

Product 1

HCID 21527996HCID 21527996, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1 part of (4(RS)-hydroxy-3,3-dimethyl-1-octynyl)trimethylsilane, 1 part of potassium fluoride and 5 parts by volume of dimethylformamide is stirred vigorously at room temperature for about 16 hours, then is diluted with ether and water. The ether layer is separated, washed with water, dried over anhydrous sodium sulfate and stripped of solvent under reduced pressure to afford 3,3-dimethyl-1-octyn-4(RS)-ol, which exhibits an infrared absorption maximum at about 3320 reciprocal centimeters.

Workup

  1. customThe ether layer is separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-8fbf6370e1fc40ee82faa4756e415ab0
Source dataset
uspto-grants-1976_06
Patent number
US03965143

Reaction notes

Loading…