Ethylparaben → Ethyl 4-(4,4-dimethyl-7-thiochromanoyloxy)benzoate

HRID 330342Notes

Reaction equation

HRID 330342 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1.O[C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=3)=[O:13])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 8434EthylparabenHCID 10868DicyclohexylcarbodiimideHCID 199355444,4-Dimethyl-7-carboxythiochroman

Product 1

HCID 19834233Ethyl 4-(4,4-dimethyl-7-thiochromanoyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 103.5 mg (0.466 mmol) of 4,4-dimethyl-7-carboxythiochroman and 77.8 mg (0.468 mmol) of ethyl 4-hydroxybenzoate in 10 ml of methylene chloride was treated sequentially with 14.2 mg (0.116 mmol) of 4-dimethylaminopyridine and 96.9 mg (0.47 mmol) of 1,3-dicyclohexylcarbodiimide. The reaction mixture was stirred at room temperature for 120 hours and then filtered and the residue washed with 10 ml of methylene chloride. The filtrate was concentrated in-vacuo and the residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes) to give the title compound as a colorless oil. PMR (CDCl3): 1.38 (6H, s), 1.42 (3H, t, J~7.1 Hz), 2.02 (2H, m), 3.08 (2H, m), 4.41 (2H, q, J~7.1 Hz), 7.29 (2H, d, J~8.7 Hz), 7.51 (1H, d, J~8.3 Hz), 7.81 1H, dd, J~8.3 Hz, 1.9 Hz), 7.95 (1H, d, J~1.9 Hz), 8.14 (2H, d, J~8.7 Hz)

Workup

  1. filtrationfiltered
  2. washthe residue washed with 10 ml of methylene chloride
  3. concentrationThe filtrate was concentrated in-vacuo
  4. customthe residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8105b5cd662a4ff2b474efa34f84938f
Source dataset
uspto-grants-1990_01
Patent number
US04895868

Reaction notes

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