Water → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-methylbut-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid

HRID 514071

反応式

HRID 514071 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=C2C2C=CC(Cl)=CC=2)=[CH:4][CH:3]=1.BrC1C=C2C(C=C(C)C(C(O)C(OCC)=O)=[C:39]2[C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=2)=CC=1.Cl(O)(=O)(=O)=O.[OH2:62]>C(OC(C)=O)(C)(C)C>[C:26]([O:25][CH:19]([C:8]1[C:7]([CH3:30])=[CH:6][C:5]2[C:4](=[CH:3][C:2]([C:3]#[C:4][C:5]([OH:62])([CH3:10])[CH3:6])=[CH:11][CH:10]=2)[C:39]=1[C:42]1[CH:43]=[CH:44][C:45]([Cl:48])=[CH:46][CH:47]=1)[C:20]([OH:22])=[O:21])([CH3:29])([CH3:27])[CH3:28]

参加物

6

反応物 4

HCID 962WaterHCID 24247Perchloric AcidHCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetateHCID 67126259Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

生成物 1

HCID 565997302-Tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-methylbut-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

Preparation of ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate: To a solution of ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate (˜2.78 mmol) in t-BuOAc (14 mL) was added perchloric acid (HClO4) (334 μL, 5.56 mmol). After 3 h, water was added. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give 877 mg of the titled compound. 1H-NMR: 400 MHz, (CDCl3) δ: 7.62 (m, 2H), 7.51 (m, 4H), 7.27 (m, 2H), 5.09 (s, 1H), 4.15 (m, 2H), 2.59 (s, 3H), 1.19 (t, J=7 Hz, 3H), 1.00 (s, 9H).

後処理

  1. customThe layers were separated
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-692f879800794bb98b51c393feb13641
出典データセット
uspto-grants-2015_08
特許番号
US09102614B2

関連ノート

読み込み中…