Sodium hydride → HCID 21434055, compound

HRID 2398787Notes

Reaction equation

HRID 2398787 reaction equation
[H-].[Na+].[CH:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])([CH3:5])[CH3:4].Br[CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=1.[Br-].[Na+]>COCCOC>[CH:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24][CH3:25])=[CH:22][CH:23]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 253881Sodium BromideHCID 5370924-IsopropoxybutanolHCID 21434045HCID 21434045, compound

Product 1

HCID 21434055HCID 21434055, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

0.320 g (7.35 millimols) of 55% sodium hydride dispersion in oil are added by portions, over the course of 15 minutes and while stirring, to 1.02 g (7.7 millimols) of 4-isopropoxybutanol and 1.82 g (7.0 millimols) of 1-(4-bromo-butyloxy)-4-(methylthio)-benzene in 20 cc of absolute 1,2-dimethoxy ethane. The mixture is stirred at 20° for 18 hours and subsequently at 60° for 6 hours. The resulting sodium bromide is suction filtered, washed with ether and the filtrate is evaporated. After chromatography of the residue on silica gel with hexane/ethyl acetate (97:3) and (95:5), 1-[4-(4-isopropoxy-butyloxy)-butyloxy]-4-(methylthio)-benzene is obtained as a colourless oil.

Workup

  1. filtrationfiltered
  2. washwashed with ether
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-f2655dd51ad449289201d246b9b78f04
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

Loading…