Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans- → (+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentane

HRID 2301762Notes

Reaction equation

HRID 2301762 reaction equation
[CH2:1]=[C:2]1[CH2:6][C@@H:5]([C:7](OC)=[O:8])[C@H:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:8][CH2:7][C@@H:5]1[CH2:6][C:2](=[CH2:1])[CH2:3][C@H:4]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 12537224Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans-HCID 21226445Aluminium lithium hydride

Product 1

HCID 18686190(+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentaneYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl(+−)-trans-4-methylene-2-phenylcyclopentanoate (5.0 g, 23 mmol) from Step A in THF (30 mL) under nitrogen was added dropwise over 10 min 1M lithium aluminum hydride (LAH) in THF (23 mL). After 2 h at RT, the excess LAH was quenched by dropwise addition of ethyl acetate and the reaction was then poured into dilute aq. HCl. The mixture was extracted twice with ether and the organic layers were washed with brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC (20-30% ethyl acetate in hexanes) to afford the title product (4.5 g) as a white solid.

Workup

  1. customthe excess LAH was quenched by dropwise addition of ethyl acetate
  2. additionthe reaction was then poured into dilute aq. HCl
  3. extractionThe mixture was extracted twice with ether
  4. washthe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by FC (20-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-23f03c385e774c859c22ed25e784b6e3
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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