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

HRID 2415183Notes

Reaction equation

HRID 2415183 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-0ff2eef8a1994025ae773ab3725ec07e
Source dataset
uspto-grants-2004_11
Patent number
US06818652B2

Reaction notes

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