Sodium Hydroxide → (E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2, 1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid

HRID 1869836ノート

反応式

HRID 1869836 の反応式
C([O:3][C:4](=[O:33])/[C:5](/[CH3:32])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[C:17]([CH:29]3[CH2:31][CH2:30]3)[C:18]3[O:25][C:22]4([CH2:24][CH2:23]4)[C:21]([CH3:26])=[C:20]([CH3:27])[C:19]=3[CH:28]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH:29]1([C:17]2[C:18]3[O:25][C:22]4([CH2:24][CH2:23]4)[C:21]([CH3:26])=[C:20]([CH3:27])[C:19]=3[CH:28]=[C:15]([C:14]#[C:13][C:10]3[CH:9]=[CH:8][C:7](/[CH:6]=[C:5](\[CH3:32])/[C:4]([OH:33])=[O:3])=[CH:12][CH:11]=3)[CH:16]=2)[CH2:30][CH2:31]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 69069630(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester2 回

生成物 1

HCID 21107275(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2, 1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

A solution of (E)-3-{4-[8-cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester (Intermediate 3, 0.06 g, 0.13 mmol) in ethanol (2 mL) was treated with a 1M solution of sodium hydroxide (0.5 mL, 0.5 mmol) and the resulting reaction mixture was heated at 55° C. for 4 h. The reaction mixture was cooled to ambient temperature and the volatiles were evaporated in vacuo to a residue that was neutralized with 5% hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid after flash column chromatography over silica gel (230-400 mesh) (0.044 g, 82%).

後処理

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe volatiles were evaporated in vacuo to a residue that
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-6b170b42b1df4be0b76f181be103fffb
出典データセット
uspto-grants-2009_12
特許番号
US07638648B2

反応ノート

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