Sodium Hydroxide → HCID 57800044, compound

HRID 2100688Notes

Reaction equation

HRID 2100688 reaction equation
[CH3:1][C:2]1[C:3]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][CH:19]=2)=[CH2:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[OH-:27].[Na+]>CC(O)(C)C>[CH3:1][C:2]1[C:3]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH2:26])=[O:27])=[CH:20][CH:19]=2)=[CH2:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57799997HCID 57799997, compound

Product 1

HCID 57800044HCID 57800044, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl-acetonitrile (15 mg, 0.044 mmol) in 1 mL of t-BuOH was added NaOH (1 mL of 2N solution, 2 mmol). The mixture was heated at 100° C. for 24 hours. After acidification and extraction with EtOAc, the organic fraction was dried over Na2SO4, filtered and concentrated in vacuo. Purification by PTLC gave 5.2 mg of the amide product.

Workup

  1. extractionAfter acidification and extraction with EtOAc
  2. dry with materialthe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by PTLC

Sources & evidence

ORD record
ord-bc99f39775b14baf8a501a09dbe2db25
Source dataset
uspto-grants-2009_08
Patent number
US07572816B2

Reaction notes

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