HCID 22640671, compound → 4,4-Dimethyl-7-(1-methylene-hexyl)-chroman

HRID 899270Notes

Reaction equation

HRID 899270 reaction equation
[CH2:1]([Li])CCC.[CH3:6][C:7]1([CH3:24])[C:16]2[C:11](=[CH:12][C:13]([C:17](=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:15]=2)[O:10][CH2:9][CH2:8]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:6][C:7]1([CH3:24])[C:16]2[C:11](=[CH:12][C:13]([C:17](=[CH2:1])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:15]=2)[O:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 22640671HCID 22640671, compoundHCID 178418339Butyllithium

Product 1

HCID 226406814,4-Dimethyl-7-(1-methylene-hexyl)-chroman

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyl triphenylphosphonium bromide (1.062 g, 2.97 mmole) in 20 mL of THF at 0° C. was treated dropwise with 1.2 mL of a 2.5M butyllithium solution. The mixture was stirred at room temperature for 30 minutes and then cooled to 0° C. A solution of 1-(4,4-dimethyl-chroman-7-yl)-hexan-1-one (0.516 g, 1.98 mmole) in 5 mL of THF was added to the ylide solution. The reaction mixture was stirred at room temperature for one hour, quenched by the addition of 25 mL water and extracted with three 25 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow solid. The product was purified by flash chromatography (SiO2, 2% ethyl acetate in hexanes) to yield 0.442 g of 4,4-dimethyl-7-(1-methylene-hexyl)-chroman as a colorless oil.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe reaction mixture was stirred at room temperature for one hour
  3. customquenched by the addition of 25 mL water
  4. extractionextracted with three 25 mL portions of ether
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow solid
  9. customThe product was purified by flash chromatography (SiO2, 2% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-498240b365534b988f537046904b4870
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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