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 514090Notes

Reaction equation

HRID 514090 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-23cf6da05916443e9d5b8c820721d82b
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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