Triethylamine → HCID 54523893, compound

HRID 361300Notes

Reaction equation

HRID 361300 reaction equation
O[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[C:7]=1[O:16][CH3:17])[CH2:3][CH:4]=[CH2:5].C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl.CCOCC>[CH3:17][O:16][C:7]1[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=1[CH:2]=[CH:3][CH:4]=[CH2:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54005412HCID 54005412, compound

Product 1

HCID 54523893HCID 54523893, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 10.30 g (43.3 mmol) of 4-hydroxy-4-(2,3,4-trimethoxyphenyl)-butene and 15 mL (107 mmol) of triethylamine in 100 mL of dichloromethane was cooled in an ice bath and 3.7 mL (47.6 mmol) of methanesulfonyl chloride was added dropwise over 5 min. The ice bath was allowed to expire and the mixture was stirred overnight. The mixture was diluted with 300 mL of ether, washed with two 100 mL portions of 5% aqueous HCl and 100 mL of saturated aqueous NaHCO3, dried over MgSO4 and the solvent removed in vacuo to leave 8.14 g of crude 1-(2,3,4-trimethoxyphenyl)-1,3-butadiene as an orange oil.

Workup

  1. washwashed with two 100 mL portions of 5% aqueous HCl and 100 mL of saturated aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-26a5114edd0740328dff9d175d207538
Source dataset
uspto-grants-1999_02
Patent number
US05866513

Reaction notes

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