Isobutylene → HCID 22351412, compound

HRID 432110Notes

Reaction equation

HRID 432110 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-bb81980aafe74bf99d9e0d663bc0a1ee
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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