Potassium Hydroxide → HCID 86636879, compound

HRID 1364172Notes

Reaction equation

HRID 1364172 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]#[C:18][Si](C)(C)C)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C@H:12]([CH:14]1[CH2:16][CH2:15]1)[CH3:13])[CH2:7]2.[OH-].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]#[CH:18])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C@H:12]([CH:14]1[CH2:16][CH2:15]1)[CH3:13])[CH2:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 66933521HCID 66933521, compound

Product 1

HCID 86636879HCID 86636879, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7-chloro-2-((S)-1-cyclopropylethyl)-5-(2-(trimethylsilyl)ethynyl)isoindolin-1-one (40.88 g, 123.17 mmol) was dissolved in 250 mL of ethanol and stirred at room temperature. To the reaction mixture was added a solution of potassium hydroxide (0.10 g, 1.85 mmol) in 20 mL of water. The reaction immediately turned black and was allowed to continue stirring for 90 minutes at room temperature. The volatiles were removed under reduced pressure and the product purified by flash chromatography on silica gel eluting with a gradient of 0 to 40% ethyl acetate in hexane. This afforded the desired product as a light tan solid (20.75 g, 69.7%). 1H NMR (300 MHz, CDCl3) δ ppm 0.34-0.50 (m, 3H) 0.58-0.69 (m, 1H) 0.93-1.07 (m, 1H) 1.34 (d, 3H) 3.22 (s, 1H) 3.76 (dq, 1H) 4.31-4.54 (m, 2H) 7.45 (s, 1H) 7.51 (s, 1H). MS ESI m/z=260 (M+H). HPLC Method B: 0.80 min.

Workup

  1. customThe reaction immediately turned black
  2. stirringto continue stirring for 90 minutes at room temperature
  3. customThe volatiles were removed under reduced pressure
  4. customthe product purified by flash chromatography on silica gel eluting with a gradient of 0 to 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-56ceb79deebf474aa8ee6a45209a281e
Source dataset
uspto-grants-2011_02
Patent number
US07888353B2

Reaction notes

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