HCID 22640688, compound → HCID 22640670, compound

HRID 899277Notes

Reaction equation

HRID 899277 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)[S: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)[S:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 22640688HCID 22640688, compoundHCID 178418339Butyllithium

Product 1

HCID 22640670HCID 22640670, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyl triphenylphosphonium bromide (2.293 g, 6.42 mmole) in 40 mL of THF at 0° C., was treated dropwise with 2.6 mL of 2.5M butyllithium. The mixture was stirred at room temperature for 30 minutes and then cooled to 0° C. A solution of 1-(4,4-dimethyl-thiochroman-7-yl)-hexan-1-one (1.183 g, 4.28 mmole) in 10 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 50 mL water and was extracted with three 50 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, 1% ethyl acetate in hexanes) to yield 0.939 g of 4,4-dimethyl-7-(1-methylene-hexyl)-thiochroman 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 50 mL water
  4. extractionwas extracted with three 50 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, 1% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7b7047c965a244f2921f3fcb732cd5d7
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

Loading…