Water → HCID 24974098, compound

HRID 1776962Notes

Reaction equation

HRID 1776962 reaction equation
[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li][CH2:23][CH2:24][CH2:25][CH3:26].[C:27]1(=O)[CH2:41][CH2:40]CCC[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.O>C1COCC1.C(Cl)Cl>[CH2:26]=[C:25]1[CH2:40][CH2:41][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:23][CH2:24]1

Participants

7

Reactant 4

HCID 962WaterHCID 10409CyclopentadecanoneHCID 638159Methyltriphenylphosphonium iodideHCID 178418339Butyllithium

Product 1

HCID 24974098HCID 24974098, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyltriphenylphosphonium iodide (12 g, 30 mmol) in THF (200 mL) was added dropwise n-BuLi (18.5 mL, 30 mmol) at 0° C. The suspension was stirred at 0° C. until a yellow color persisted, and then cyclopentadecanone, 48, (2.21 g, 9.8 mmol) was added as a solution in THF (20 mL). The mixture was allowed to warm to room temperature and stirred overnight. Upon completion, H2O was added to quench any remaining n-BuLi and any precipitates were filtered off. The filtrate was concentrated in vacuo and the residue was redissolved in CH2Cl2, washed three times with deionized H2O. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and then concentrated under reduced pressure to give a pale red oil. After column chromatography (Rf=0.9, 10% CH2Cl2/90% hexanes) 51 was isolated as a pale yellow oil (1.5 g, 69%). 1H NMR (CDCl3) δ 4.65 (s, 2H), 1.96 (t, 4H), 1.37 (m, 4H), 1.27-1.25 (m, 20H).48

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customto quench any remaining n-BuLi
  4. filtrationany precipitates were filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionthe residue was redissolved in CH2Cl2
  7. washwashed three times with deionized H2O
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto give a pale red oil

Sources & evidence

ORD record
ord-7087464e4ae54089918d7655c76d4964
Source dataset
uspto-grants-2016_02
Patent number
US09266815B2

Reaction notes

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