Trifluoroacetic acid → (2E)-3-{4-[Cyclopentylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoic acid

HRID 229129ノート

反応式

HRID 229129 の反応式
[C:1]1(=[C:6]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17]C(C)(C)C)=[O:16])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[C:1]1(=[C:6]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 689778841,1-Dimethylethyl (2E)-3-{4-[cyclopentylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoate

生成物 1

HCID 11255664(2E)-3-{4-[Cyclopentylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To an ice-water cooled solution of 1,1-dimethylethyl (2E)-3-{4-[cyclopentylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoate (4) (0.28 g, 0.74 mmol) in dichloromethane (5 mL) was slowly added trifluoroacetic acid (5 mL) with stirring under a nitrogen atmosphere. After 1 h, the reaction mixture was concentrated in vacuo to give a solid. The solid was dissolved in dichloromethane and the solution was concentrated in vacuo to give a pale tan solid. The solid was triturated with diethyl ether and filtered to give the acrylic acid as an off-white solid. The solid was dried overnight under vacuum at 70° C., however, 1H NMR indicated that solvent remained in the sample. The solid was dissolved in methanol and the solution was concentrated in vacuo to give an oil. The oil was dissolved in methanol and the solution was concentrated in vacuo under high vacuum at 60° C. to give an oil. Dichloromethane was added to the oil and crystallization was induced with the aid of a spatula. The suspension was filtered and the solid was dried in a vacuum oven overnight at 70° C. to give 0.072 g (30%) of compound 5 as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 1.60 (m, 4H), 2.30 (m, 4H), 6.44 (d, J=15.9 Hz, 1H), 6.67 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.2 Hz, 2H), 7.53 (d, J=15.9 Hz, 1H), 7.57 (d, J=8.3 Hz, 2H), 9.32 (s, 1H). The compound was silated prior to EI analysis. HRMS (EI) Calcd for C27H36Si2O3: 464.2203 (M+.). Found: 464.2210.

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto give a solid
  3. concentrationthe solution was concentrated in vacuo
  4. customto give a pale tan solid
  5. customThe solid was triturated with diethyl ether
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-b4f49289c530446e88b311a5dee73b54
出典データセット
uspto-grants-2009_07
特許番号
US07560589B2

反応ノート

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