Aluminium lithium hydride → 4-(2-Fluorobenzyl)cyclohexylmethanol

HRID 1015363Notes

Reaction equation

HRID 1015363 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH2:13][CH2:12]1)=O>O1CCCC1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][CH:14]1[CH2:13][CH2:12][CH:11]([CH2:9][OH:8])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 673020364-(2-Fluorobenzyl)cyclohexanecarboxylic Acid Methyl Ester

Product 1

HCID 673023774-(2-Fluorobenzyl)cyclohexylmethanolYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a dry 50 mL 1 neck round bottom flask, lithium aluminium hydride (150 mg; 4.0 mmol) was suspended in dry tetrahydrofuran at 0° C. under nitrogen flow. Dissolved 4-(2-fluorobenzyl)cyclohexanecarboxylic acid methyl ester was added over 2 minutes and mixture was allowed to warm to room temperature. After 3 hours at room temperature, Reaction was quenched with at 0° C. with 0.15 mL of water. After 20 minutes, 0.15 mL of 15% NaOH was added. Finally, 0.45 mL of water was added and continued to stir at 0° C. for 20 minutes. White precipitate was filtered off and rinsed twice with 10 mL ethyl acetate each. Filtrate was concentrated to an oil. Oil was purified by flash chromatography (13:1) and eluted with 10-15% ethyl acetate in hexanes to give 161 mg of title compound. (73% yield).

Workup

  1. customReaction
  2. customwas quenched with at 0° C. with 0.15 mL of water
  3. waitAfter 20 minutes
  4. addition0.15 mL of 15% NaOH was added
  5. additionFinally, 0.45 mL of water was added
  6. filtrationWhite precipitate was filtered off
  7. washrinsed twice with 10 mL ethyl acetate each
  8. concentrationFiltrate was concentrated to an oil
  9. customOil was purified by flash chromatography (13:1)
  10. washeluted with 10-15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a812b8824a94465d917023dc5dcc51d1
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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