Trimethyl orthoformate → HCID 67490749, compound

HRID 1919861Notes

Reaction equation

HRID 1919861 reaction equation
[CH:1]1([S:7][C:8]2[CH:15]=[CH:14][C:11](C=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:16][O:17][CH:18](OC)[O:19][CH3:20].C[O-].[Na+]>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:8]1([S:7][C:1]2[CH:6]=[CH:5][C:4]([CH:18]([O:19][CH3:20])[O:17][CH3:16])=[CH:3][CH:2]=2)[CH2:15][CH2:14][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 9005Trimethyl orthoformateHCID 10942334Sodium MethoxideHCID 19616685HCID 19616685, compound

Product 1

HCID 67490749HCID 67490749, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(cyclohexylthio)benzaldehyde (215 mg, 0.976 mmol) in methanol (4 mL) was added trimethylorthoformate (130 μL, 1.19 mmol) and p-toluenesulfonic acid (15 mg, 0.079 mmol), and the resulting solution stirred at room temperature for 72 hours. Sodium methoxide solution (25 wt %, 18 μL) was then added to the solution, and the volatiles removed in vacuo to afford crude cyclohexyl(4-(dimethoxymethyl)phenyl)sulfane (˜265 mg, quantitative yield) which was used directly without further purification.

Workup

  1. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-fa2961266dcf48d3b834f91735c3cd6e
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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