Potassium Phosphate, Tribasic → HCID 59864959, compound

HRID 1958561Notes

Reaction equation

HRID 1958561 reaction equation
Br[C:2]([C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10])=[C:3]([CH3:5])[CH3:4].[S:12]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(O)CCC>[S:12]1[CH:16]=[CH:15][C:14]([C:2]([C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10])=[C:3]([CH3:5])[CH3:4])=[CH:13]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acidHCID 59864982HCID 59864982, compound

Product 1

HCID 59864959HCID 59864959, compoundYield 61.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 2631-ButanolSolvent

Procedure

To a magnetically stirred solution of 3-bromo-2-methyl-oct-2-en-4-one (5 gram, 20.54 mmol) (Intermediate IIIc-1) in nitrogen-degassed n-butanol (50 ml) was successively added thiophene-3-boronic acid (3.94 gram, 30.80 mmol), palladium(II)acetate (46.11 mg, 0.21 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (S-Phos) (168.6 mg, 0.41 mmol) and K3PO4 (8.72 g, 41.07 mmol) and the resulting mixture was reacted at 100° C. for 2 hours. The mixture was concentrated in vacuo and purified by sepacore chromatography (40×150 mm column), eluant: (Gradient: eluant 1: petroleum ether (40-60); Eluant 2: petroleum ether (40-60)/diethyl ether=95/5 (v/v)) to give 3-(3-thienyl)-2-methyl-oct-2-en-4-one (2.80 gram, 55%). 1H-NMR (400 MHz, CDCl3) δ 0.83 (t, J=7, 3H), 1.17-1.27 (m, 2H), 1.45-1.54 (m, 2H), 1.72 (s, 3H), 1.97 (s, 3H), 2.30 (t, J=7.4, 2H), 6.92 (br d, J=5, 1H), 7.04 (br d, J=3, 1H), 7.33 (dd, J=5 and 3, 1H).

Workup

  1. customthe resulting mixture was reacted at 100° C. for 2 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by sepacore chromatography (40×150 mm column), eluant

Sources & evidence

ORD record
ord-78115225de5f437899fb5aaef7b01794
Source dataset
uspto-grants-2013_04
Patent number
US08410135B2

Reaction notes

Loading…