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

HRID 514090

反応式

HRID 514090 の反応式
[C:1]([O:5][CH:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][C:14]([C:21]#[C:22][C:23]([OH:26])([CH3:25])[CH3:24])=[CH:15][CH:16]=2)[C:11]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]>CCO.[Rh]>[C:1]([O:5][CH:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][C:14]([CH2:21][CH2:22][C:23]([OH:26])([CH3:24])[CH3:25])=[CH:15][CH:16]=2)[C:11]=1[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 1

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

生成物 1

HCID 566001332-Tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-methylbutyl)-3-methylnaphthalen-2-yl)acetic acid収率 87.8%

試薬・触媒・溶媒 2

HCID 23948Rhodium触媒HCID 702Ethanol溶媒

実験手順

To a solution of 2-tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-methylbut-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid (8 mg, 0.017 mmol) in EtOH (1 mL) was added rhodium on alumina (2 mg). The reaction was flushed with hydrogen gas and then stirred under and hydrogen atmosphere for 1 h. The reaction was filtered and concentrated in vacuo to give 7 mg of the titled compound. 1H-NMR: 400 MHz, (CD3OD) δ: 7.68 (d, J=8 Hz, 1H), 7.63 (m, 1H), 7.61 (s, 1H), 7.53 (m, 2H), 7.30 (m, 2H), 7.05 (s, 1H), 5.12 (s, 1H), 2.65 (m, 2H), 2.59 (s, 3H), 1.66 (m, 2H), 1.19 (s, 6H), 0.96 (s, 9H). HPLC (Kinetex 2.6u, 50×4.6 mm, 2-100% MeCN/H2O+0.05% HOAc, 4.0 min run): tR (min)=3.52.

後処理

  1. customThe reaction was flushed with hydrogen gas
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-23cf6da05916443e9d5b8c820721d82b
出典データセット
uspto-grants-2015_08
特許番号
US09102614B2

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