Potassium Hydroxide → 2-(Cyclohexylmethyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

HRID 538858Notes

Reaction equation

HRID 538858 reaction equation
[C:1]1(=[O:13])[C:12]2[C:4](=[CH:5][C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.[CH:14]1([CH:20]=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[OH-].[K+].[H][H]>[Pd].C(O)C>[CH:14]1([CH2:20][CH:2]2[CH2:3][C:4]3[C:12](=[CH:11][C:10]4[CH2:9][CH2:8][CH2:7][C:6]=4[CH:5]=3)[C:1]2=[O:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 16275CyclohexanecarboxaldehydeHCID 109318913,5,6,7-tetrahydro-s-indacen-1(2H)-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 666155982-(Cyclohexylmethyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In argon atmosphere, a 250 ml Berghof stainless steel autoclave with PTFE leaner was charged with 25.0 g (0.145 mol) of 3,5,6,7-tetrahydro-s-indacen-1(2H)-one, 20.0 g (0.178 mmol) of cyclohexanecarbaldehyde, 2.0 g (0.036 mol) of potassium hydroxide, 2.0 g of 10% Pd on charcoal and 150 ml of 96% ethanol. This reactor was flashed by hydrogen, and then hydrogen was fed to a pressure of 3 atm. This mixture was stirred for 3 h at room temperature. The resulting mixture was filtered through glass frit (G3), and the precipitate was additionally washed by 50 ml of ethanol. The filtrate was evaporated to dryness, and 500 ml was added to the residue. The crude product was extracted by 3×200 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: dichloromethane). Yield 36.5 g (94%).

Workup

  1. filtrationThe resulting mixture was filtered through glass frit (G3)
  2. washthe precipitate was additionally washed by 50 ml of ethanol
  3. customThe filtrate was evaporated to dryness, and 500 ml
  4. additionwas added to the residue
  5. extractionThe crude product was extracted by 3×200 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over Na2SO4
  8. customevaporated to dryness
  9. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: dichloromethane)

Sources & evidence

ORD record
ord-042678fcb84347ea8e596dd9edbe418d
Source dataset
uspto-grants-2014_10
Patent number
US08865848B2

Reaction notes

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