Triethylamine → HCID 54396231, compound

HRID 1248787Notes

Reaction equation

HRID 1248787 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([OH:17])[CH:10]=1)=[O:7].[CH2:18](OC1C=C(O)C=CC=1OC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O1C=CC=C1C(Cl)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1)=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 135310983-(Benzyloxy)-4-methoxyphenolHCID 536654323-Hydroxy-4-methoxyphenyl 2-furancarboxylate

Product 1

HCID 54396231HCID 54396231, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound 3-hydroxy-4-methoxyphenyl 2-furoate was made as follows. An amount of 2.00 gms. of 3-benzyloxy-4-methoxyphenol, 1.00 gms. of triethylamine and 0.10 gms of 4-dimethylaminopyridine were dissolved in 100 ml. of methylene chloride at 0° C. and stirred. To the mixture was added 1.16 gms. of 2-furoyl chloride and the mixture was stirred overnight. The mixture was then washed with equal volumes of 1M hydrochloric acid, saturated sodium bicarbonate and water. The mixture was then dried over magnesium sulfate and the solvent evaporated to yield 3-benzyloxy-4-methoxyphenyl 2-furoate.

Workup

  1. additionTo the mixture was added 1.16 gms
  2. washThe mixture was then washed with equal volumes of 1M hydrochloric acid, saturated sodium bicarbonate and water
  3. dry with materialThe mixture was then dried over magnesium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-16a9c73d18f746df95317f6d5d164f3c
Source dataset
uspto-grants-1986_12
Patent number
US04626442

Reaction notes

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