Methanol → 4-Benzyloxy-3-ethylsulfinylphenol

HRID 23566Notes

Reaction equation

HRID 23566 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[S:16]([CH3:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([N-]C(C)C)(C)C.[Li+].CI.CO>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[S:16]([CH2:18][CH3:19])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 225744604-Benzyloxy-3-methylsulfinylphenol

Product 1

HCID 225744554-Benzyloxy-3-ethylsulfinylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.4 g of 4-benzyloxy-3-methylsulfinylphenol pmb (1.05 mmol) in 40 ml of tetrahydrofuran is cooled to −50° C. and 0.784 ml of a dimolar solution of lithium diisopropylamide (1.57 mmol) in tetrahydrofuran is then added. The reaction mixture is stirred for 15 minutes and 0.13 ml of methyl iodide (1.1 mmol) is added. After stirring for 15 minutes, methanol is added and the solvents are evaporated off under reduced pressure. The 4-benzyloxy-3-ethylsulfinylphenol pmb is obtained in the form of a white solid (0.3 g, 72%) after purification on silica gel (40 g SiO2, eluent: 4/1 heptane/ethyl acetate)

Workup

  1. stirringAfter stirring for 15 minutes
  2. customthe solvents are evaporated off under reduced pressure

Sources & evidence

ORD record
ord-ddd2918f70da4a6ca26f83d6f354b3bb
Source dataset
uspto-grants-2005_02
Patent number
US06852736B2

Reaction notes

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