tert-Butyl acrylate → HCID 68450766, compound

HRID 646463Notes

Reaction equation

HRID 646463 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21](Br)=[CH:20][C:19]=1[C:33]1[O:37][N:36]=[C:35]([CH3:38])[C:34]=1[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:47]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])(=[O:50])[CH:48]=[CH2:49]>C(O)CCC.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>[C:52]([O:51][C:47](=[O:50])[CH:48]=[CH:49][C:21]1[CH:20]=[C:19]([C:33]2[O:37][N:36]=[C:35]([CH3:38])[C:34]=2[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:18]([O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:23][C:22]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:55])([CH3:54])[CH3:53]

Participants

6

Reactant 3

HCID 15458tert-Butyl acrylateHCID 81531DiisopropylethylamineHCID 59264722HCID 59264722, compound

Product 1

HCID 68450766HCID 68450766, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 178424406HCID 178424406, compoundCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

Diisopropylethyl amine (1 ml, 5.7 mmol) was added to a suspension of 5-(2,4-Bis-benzyloxy-5-bromo-phenyl)-4-(4-methoxy-phenyl)-3-methyl-isoxazole (0.56 g, 1.0 mmol) in tert-butyl acrylate (1 ml, 6.8 mmol) and 1-butanol (8 ml) under a nitrogen atmosphere. Dichlorobis(tri-o-tolylphosphine)palladium (II) (cat.) was added and the suspension heated, 140° C. for ˜18 hrs., to give a yellow/green solution. The solution was allowed to cool and concentrated to a yellow/green gum. The crude product was purified by column chromatography, silica, eluting with ethyl acetate/hexane (1:9), to give 3-{2,4-Bis-benzyloxy-5-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-phenyl}-acrylic acid tert-butyl ester as a yellow/green gum (315 mg). Starting material (170 mg) was recovered.

Workup

  1. custom, to give a yellow/green solution
  2. temperatureto cool
  3. concentrationconcentrated to a yellow/green gum
  4. customThe crude product was purified by column chromatography, silica
  5. washeluting with ethyl acetate/hexane (1:9)

Sources & evidence

ORD record
ord-f9c83b66614f40cfb9de2b697f81f4a5
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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