Aluminium lithium hydride → (1-Phenylcyclopent-3-enyl)methanol

HRID 1178844Notes

Reaction equation

HRID 1178844 reaction equation
[C:1]1([C:7]2([C:12](OC)=[O:13])[CH2:11][CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:1]1([C:7]2([CH2:12][OH:13])[CH2:11][CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23533669Methyl 1-phenylcyclopent-3-enecarboxylate

Product 1

HCID 57087982(1-Phenylcyclopent-3-enyl)methanolYield 100.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 1-phenylcyclopent-3-enecarboxylate (298 mg) in ether (10 mL) at 0° C. was added lithium aluminum hydride (1.0 M solution in ether, 1.48 mL), and the resulting suspension was stirred at 0° C. for 30 min. The reaction was quenched with saturated sodium sulfate and then diluted with ether (100 mL). Anhydrous sodium sulfate was added, and the ether solution was filtered. The filtrate was evaporated in vacuo to give the title compound as an oil (257 mg). 1H NMR (400 MHz, CDCl3) δ 2.70 (4H, s), 3.54 (2H, d, J=5.6 Hz), 5.75 (1H, s), 7.22-7.35 (5H, m).

Workup

  1. customThe reaction was quenched with saturated sodium sulfate
  2. additiondiluted with ether (100 mL)
  3. additionAnhydrous sodium sulfate was added
  4. filtrationthe ether solution was filtered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-fca808d238b64be4892ca9a707ac7152
Source dataset
uspto-grants-2007_10
Patent number
US07276631B2

Reaction notes

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