Aluminium lithium hydride → [1-(Hydroxymethyl)-4-methylene-cyclohexyl]methanol

HRID 2040896Notes

Reaction equation

HRID 2040896 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]=[C:8]1[CH2:13][CH2:12][C:11]([C:19](OCC)=[O:20])([C:14](OCC)=[O:15])[CH2:10][CH2:9]1>CCOCC>[OH:15][CH2:14][C:11]1([CH2:19][OH:20])[CH2:12][CH2:13][C:8](=[CH2:7])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 57493861HCID 57493861, compound

Product 1

HCID 66603642[1-(Hydroxymethyl)-4-methylene-cyclohexyl]methanolYield 92.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (0.166 g, 4.4 mmol) in anhydrous Et2O (10 mL) stirred a 0° C. was added a solution of Compound 100a (100 mg, 2.08 mmol) in Et2O (10 mL). The reaction mixture was stirred at r.t. for 2 h. Additional 0.5 equivalents of LiAlH4 were added and the reaction was stirred at r.t. for 1 h. Afterwards, it was quenched, by adding THF/H2O (2 mL:1.3 mL), then 2N HCl (30 mL). Extraction with EtOAc, drying over Na2SO4 and evaporation to dryness afforded a crude, that was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Dichloromethane-Methanol gradient from 1:0 to 95:5) to give the title compound as a white solid. Yield: 92.1%.

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 2 h
  2. stirringthe reaction was stirred at r.t. for 1 h
  3. customAfterwards, it was quenched
  4. additionby adding THF/H2O (2 mL:1.3 mL)
  5. extractionExtraction with EtOAc
  6. dry with materialdrying over Na2SO4 and evaporation to dryness
  7. customafforded a crude, that
  8. customwas purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Dichloromethane-Methanol gradient from 1:0 to 95:5)

Sources & evidence

ORD record
ord-b43a2641476c4e6a9ad2e7dc259daa1b
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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