Lithium Chloride → HCID 54456954, compound

HRID 51163Notes

Reaction equation

HRID 51163 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8](Br)=[C:9]([CH3:12])[CH:10]=2)[C:5](=[O:14])[CH2:4][CH2:3]1.[Cl-].[Li+].C([Sn](CCCC)(CCCC)[C:23]([C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=1)=[CH:24][Si:25]([CH3:28])([CH3:27])[CH3:26])CCC>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][C:9]1[C:8]([C:23]([C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:38][CH:39]=2)=[CH:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[CH:7][C:6]2[C:5](=[O:14])[CH2:4][CH2:3][C:2]([CH3:15])([CH3:1])[C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 121061407-bromo-4,4,6-trimethyl-3,4-dihydro-2H-naphthalen-1-oneHCID 69886944Ethyl 4-(1-(tributylstannyl)-2-(trimethylsilyl)-ethen-1-yl)-benzoate

Product 1

HCID 54456954HCID 54456954, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A solution of 1,2,3,4-tetrahydro-4,4,6-trimethyl-1-oxo-7-bromonaphthalene (8.5 g, 31.8 mmol) was purged with argon (2×). Lithium chloride (4.0 g), copper iodide (0.860 g), tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.6 mmol) and ethyl 4-(1-(tributylstannyl)-2-(trimethylsilyl)-ethen-1-yl)-benzoate (24.0 g, 44.5 mmol) were then added and the resulting mixture was again purged with argon. The mixture was heated to 80° C. for ˜4 hours, and then cooled to room temperature. The mixture was poured into cold water (1 L) and was diluted with ethyl ether. The organic phase was separated, washed with cold water (2×1 L), saturated sodium bicarbonate (1 L), brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (8×15 cm, 0 to 5% ethyl acetate/toluene) to give the title material which was triturated in hexane (12.2 g, 88%).

Workup

  1. customthe resulting mixture was again purged with argon
  2. temperaturecooled to room temperature
  3. additionThe mixture was poured into cold water (1 L)
  4. additionwas diluted with ethyl ether
  5. customThe organic phase was separated
  6. washwashed with cold water (2×1 L), saturated sodium bicarbonate (1 L), brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography (8×15 cm, 0 to 5% ethyl acetate/toluene)

Sources & evidence

ORD record
ord-5325d4890abb4367947f719f45df01a5
Source dataset
uspto-grants-2004_03
Patent number
US06713515B2

Reaction notes

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