Lithium Chloride → HCID 89650431, compound

HRID 2275989Notes

Reaction equation

HRID 2275989 reaction equation
[CH3:1][C:2]1([CH3:27])[C:7]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[C:6](OS(C(F)(F)F)(=O)=O)[CH2:5][CH2:4][CH2:3]1.[CH2:28]([SnH3])[CH:29]=[CH2:30].[Cl-].[Li+]>O1CCOCC1>[CH2:30]([C:6]1[CH2:5][CH2:4][CH2:3][C:2]([CH3:27])([CH3:1])[C:7]=1[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH:29]=[CH2:28]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 71334751HCID 71334751, compoundHCID 89650010HCID 89650010, compound

Product 1

HCID 89650431HCID 89650431, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of benzyl 2-[6,6-dimethyl-2-(trifluoromethylsulfonyloxy)cyclohexen-1-yl]acetate (2.30 g, 5.66 mmol) in dioxane (10 mL) was purged with argon. Then, allyl stannane (2.10 mL, 6.79 mmol), palladium triphenylphosphine tetrakis (327 mg, 0.28 mmol) and lithium chloride (360 mg, 8.49 mmol) were added. The solution was heated to reflux for 7 h and was then concentrated to give a crude yellow oil, which was purified by flash chromatography eluting with cyclohexane and ethyl acetate (25/1) to give the title compound as a colourless oil (1.55 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.33-7.40 (5H, m), 5.72 (1H, ddt, J=16.8, 10.5, 6.2 Hz), 5.11 (2H, s), 4.97 (1H, dt, J=16.8, 1.5 Hz), 4.96 (1H, dt, J=10.5, 1.5 Hz), 3.11 (2H, s), 2.71 (2H, d, J=6.2 Hz), 2.00 (2H, t, J=6.2 Hz), 1.58-1.65 (2H, m), 1.46-1.50 (2H, m), 0.97 (6H, s) ppm.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 7 h
  3. concentrationwas then concentrated
  4. customto give a crude yellow oil, which
  5. customwas purified by flash chromatography
  6. washeluting with cyclohexane and ethyl acetate (25/1)

Sources & evidence

ORD record
ord-3ae7e7f6928f4bdd93f28c34e9d9fba6
Source dataset
uspto-grants-2015_09
Patent number
US09131688B2

Reaction notes

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