HCID 13446689, compound → HCID 86691657, compound

HRID 2406869Notes

Reaction equation

HRID 2406869 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]12(C(=O)C3C[CH:11]1[CH2:12][CH2:13]3)[CH2:10][CH2:9][CH2:8][CH2:7]2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:4]=[C:3]1[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:11]2[CH2:1][CH:2]1[CH2:13][CH2:12]2

Participants

5

Reactant 2

HCID 13446689HCID 13446689, compoundHCID 178418339Butyllithium

Product 1

HCID 86691657HCID 86691657, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (methyl)triphenylphosphonium bromide (17.6 g, 48.4 mmol) in THF (100 mL) at −78° C. was added n-butyllithium (18.1 mL of 2.5 M solution in THF, 45 mmol) and the mixture was stirred 30 min. To this mixture was added spiro[bicyclo[2.2.1]heptane-2,1′-cyclopentan]-3-one (5.30 g, 32.3 mmol), and the reaction was stirred at ambient temperature for 18 h. Hexanes (200 mL) were added, and the mixture was filtered. The filtrate was concentrated, and the residue was purified on an 80 g silica gel column, eluting with hexanes, to obtain 3-methylenespiro[bicyclo[2.2.1]heptane-2,1′-cyclopentane] (4.80 g, 91.7%) as oil.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 18 h
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified on an 80 g silica gel column
  5. washeluting with hexanes

Sources & evidence

ORD record
ord-18159aee9fba4b4ab54d681e6da9d44d
Source dataset
uspto-grants-2014_08
Patent number
US08809397B2

Reaction notes

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