Sodium Hydroxide → HCID 21055336, compound

HRID 2215266Notes

Reaction equation

HRID 2215266 reaction equation
Br[CH2:2][C@@H:3]([CH3:6])[CH2:4][OH:5].[OH-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17]>O>[CH3:6][C@H:3]([CH2:2][S:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][CH3:9])[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23642ThioguaiacolHCID 10986449(S)-(+)-3-Bromo-2-methyl-1-propanol

Product 1

HCID 21055336HCID 21055336, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.2 ml (0.021 mol) of 3-bromo-2-(S)-methyl-1-propanol are introduced into a round-bottomed flask kept under an inert atmosphere. 20 ml of an aqueous sodium hydroxide solution (1N) are added dropwise, followed by 2.3 ml (0.019 mol) of 2-methoxythiophenol. The mixture is brought to 90° C. for 4 hours and is then cooled to ambient temperature. 50 ml of water are then added and the mixture is extracted with dichloromethane. The combined organic phases are washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=99:1). 4 g (0.019 mol) of the title compound (XXb-1) are recovered in the form of a colorless oil.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=99:1)

Sources & evidence

ORD record
ord-ffb14ca1d77e45778e3c3835d462584c
Source dataset
uspto-grants-2006_09
Patent number
US07109234B2

Reaction notes

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