1,2-Dimethoxyethane → 4-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester

HRID 2371278Notes

Reaction equation

HRID 2371278 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])Br)=[CH:6][CH:5]=1.[CH2:24]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)[CH:25]([CH3:27])[CH3:26].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C.O.C(O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:31]2[CH:32]=[CH:33][C:28]([CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:29][CH:30]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2773472(4-Isobutylphenyl)boronic acidHCID 866697884-(2-Benzyloxycarbonyl-2-bromo-vinyl)-benzoic acid methyl ester

Product 1

HCID 674864534-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

4-(2-Benzyloxycarbonyl-2-bromo-vinyl)-benzoic acid methyl ester (2.0 g, 5.33 mmol) was added to a 100 mL RB flask containing 4-isobutylphenylboronic acid (2.85 g, 15.99 mmol), sodium carbonate (2.83 g, 26.65 mmol), and dichlorobis(tri-o-tolylphosphine)palladium(II) (544 mg, 0.69 mmol). Dimethoxyethane (16 mL), ethanol (8 mL), and water (4 mL) were added, and the reaction was stirred at 120° C. for 1 hour at which point TLC analysis indicated that the reaction had gone to completion. The reaction was filtered hot through celite and concentrated to dryness. Purification by flash column chromatography was performed on an ISCO Sg-100c system, using a 40 gram pre-packed column and eluting with a linear gradient of ethyl acetate in hexanes starting at 10% EtOAc and ending at 40% EtOAc over 22 minutes. This afforded the desired product, 4-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester as a pale oil, 1.8 g, 79%. LC-MS m/z=429 [C28H28O4+H]+.

Workup

  1. filtrationThe reaction was filtered hot through celite and
  2. concentrationconcentrated to dryness
  3. customPurification by flash column chromatography
  4. washeluting with a linear gradient of ethyl acetate in hexanes starting at 10% EtOAc
  5. waitending at 40% EtOAc over 22 minutes

Sources & evidence

ORD record
ord-6f09f8fab0cf463d8307dc9e8001a39c
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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