Isobutylene → HCID 22351412, compound

HRID 896887Notes

Reaction equation

HRID 896887 reaction equation
[CH3:1][C:2]([CH3:4])=[CH2:3].B1C2CCCC1CCC2.[CH2:14]([O:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24](OS(C(F)(F)F)(=O)=O)[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH2:14]([O:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 8255IsobutyleneHCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 10739136HCID 10739136, compound

Product 1

HCID 22351412HCID 22351412, compoundYield 31%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a condensed liquid 2-methyl-1-propene in THF (10 mL) at −78° C. was added 0.5 M 9-BBN (3 mL, 1.5 mmol), the mixture was allowed to warm up to room temperature with stirring. The mixture was transferred via a syringe to a degassed solution containing the compound of Example 206 (0.5 g, 1.3 mmol), Pd(dppf)Cl2 (82 mg, 0.1 mmol), K2CO3 (0.23 g, 1.7 mmol), water (2 mL) in DMF (21 mL). The resulting mixture was heated at 60° C. overnight. After removal of solvent, the residue was purified by chromatography to afford the title compound (0.11 g, 31% yield). 1HNMR Chloroform-d δ 0.85 (d, 6H), 1.75-1.80 (m, 1H), 2.88 (d, 2H), 3.78 (s, 3H), 5.13 (s, 2H), 6.71-6.80 (m, 2H), 7.30-7.41 (m, 5H), 7.90 (d, 1H). Rf=0.65 ethyl acetate/hexane (1/9).

Workup

  1. customThe mixture was transferred via a syringe to a degassed solution
  2. temperatureThe resulting mixture was heated at 60° C. overnight
  3. customAfter removal of solvent
  4. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-9f6148a9dc44411a98e6b9dde62a1c07
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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