(+-)-trans4-Methylene-2-phenylcyclopentanoic acid → (+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentane

HRID 1634267Notes

Reaction equation

HRID 1634267 reaction equation
[CH2:1]=[C:2]1[CH2:6][C@@H:5]([C:7](O)=[O:8])[C@H:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 18686197(+-)-trans4-Methylene-2-phenylcyclopentanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 18686190(+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentaneYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (+−)-trans-4-methylene-2-phenylcyclopentanoic acid (26 g, 129 mmol) from Step B1 in THF (600 mL) under nitrogen at −10° C. was added dropwise over 15 min 1M lithium aluminum hydride (LAH) in THF (193 mL, 193 mmol). After 16 h at rt, the excess LAH was quenched by dropwise addition of acetone 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% ethyl acetate in hexanes) to afford the title product (23.8 g) which was the same as in Method A.

Workup

  1. customthe excess LAH was quenched by dropwise addition of acetone
  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% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-65d6a05dbc9c435f817cc76d9d38027f
Source dataset
uspto-grants-2003_01
Patent number
US06506777B1

Reaction notes

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