Triethylamine → 2-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate

HRID 1249958

Reaction equation

HRID 1249958 reaction equation
[CH3:1][C:2](=[CH2:22])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O-:19])=[O:18])=[CH:15][CH:14]=1)=[O:4].S(Cl)(Cl)=O.O[C:28]1[CH:39]=[CH:38][C:31]([CH:32]=[CH:33][C:34]([O:36][CH3:37])=[O:35])=[CH:30][C:29]=1[O:40][CH3:41].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[CH3:22][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:28]2[CH:39]=[CH:38][C:31](/[CH:32]=[CH:33]/[C:34]([O:36][CH3:37])=[O:35])=[CH:30][C:29]=2[O:40][CH3:41])=[O:18])=[CH:20][CH:21]=1)=[O:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 16830Methyl 4-hydroxy-3-methoxy-cinnamateHCID 24386Thionyl ChlorideHCID 70216454-[6-(2-Methyl-acryloyloxy)-hexyloxy]-benzoate

Product 1

HCID 183291832-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoateYield 50.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

8.5 g (0.028 mol) of 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were treated with 6 ml of thionyl chloride and 3 drops of DMF and the mixture was heated to 90° C. for 2 hours. The excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum. The residual acid chloride was taken up in 20 ml of dichloromethane and slowly added dropwise at 0° C. to a solution of 5.25 g (0.025 mol) of methyl 4-hydroxy-3-methoxy-cinnamate and 4.25 ml of triethylamine in 25 ml of THF. The batch was stirred at room temperature overnight, filtered and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel with dichloromethane/diethyl ether (19:1) and subsequently by recrystallization from ethanol/THF. 6.31 g of 2-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were isolated as a white powder; m.p. 92-94° C.

Workup

  1. customThe excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum
  2. filtrationfiltered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel with dichloromethane/diethyl ether (19:1) and subsequently by recrystallization from ethanol/THF

Sources & evidence

ORD record
ord-2503be71934b4182838359b3d2eb075a
Source dataset
uspto-grants-2002_01
Patent number
US06335409B1

Linked notes

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