Dichloromethane → 2-(3-Methoxybenzyl)benzenethiol

HRID 1987481Notes

Reaction equation

HRID 1987481 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]CC2C(OC)=CC(OC)=CC=2OC)O)[CH:6]=[CH:7][CH:8]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>CCCCCC.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68643652(3-Methoxyphenyl)(2-(2,4,6-trimethoxybenzylthio)phenyl)methanol

Product 1

HCID 686436202-(3-Methoxybenzyl)benzenethiolYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

0.288 g (3-methoxyphenyl)(2-(2,4,6-trimethoxybenzylthio)phenyl)methanol (K) (0.68 mmol) was treated with a solution of triethylsilane:TFA:DCM 0.3 ml:1 ml:10 ml. The mixture was stirred overnight at ambient temperature before the addition of water. The mixture was extracted with DCM, brine, dried over magnesium sulfate and concentrated. Flash silica chromatography (hexane:ethyl acetate 90:10) afforded 0.12 g product (0.52 mmol, 77% yield).

Workup

  1. extractionThe mixture was extracted with DCM, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e4627e0714af42b181261cc2b0b9c2b4
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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