Benzcatechinborane → N,N-diethyl (E)-3-[3-(3-hydroxypropyl)4-(1-phenylethoxy)-phenyl]-but-2-enamide

HRID 1596718Notes

Reaction equation

HRID 1596718 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[C:4](=[O:26])/[CH:5]=[C:6](/[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[C:10]([CH2:23][CH:24]=[CH2:25])[CH:9]=1)\[CH3:7])[CH3:2].[B]1OC2C(=CC=CC=2)[O:30]1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C1COCC1>[CH2:27]([N:3]([CH2:1][CH3:2])[C:4](=[O:26])/[CH:5]=[C:6](/[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])=[C:10]([CH2:23][CH2:24][CH2:25][OH:30])[CH:9]=1)\[CH3:7])[CH3:28]

Participants

5

Reactant 2

HCID 6327445BenzcatechinboraneHCID 86757413N,N-diethyl (E)-3-[3-allyl-4-(1-phenylethoxy)-phenyl]-but-2-enamide

Product 1

HCID 86757415N,N-diethyl (E)-3-[3-(3-hydroxypropyl)4-(1-phenylethoxy)-phenyl]-but-2-enamide

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N,N-diethyl (E)-3-[3-allyl-4-(1-phenylethoxy)-phenyl]-but-2-enamide (2.61 g, 6.92 mmol) and Wilkinson's catalyst (tris(triphenylphosphine)rhodium (I) chloride, 64 mg, 0.069 mmol) in THF(40 mL) at 0° is added a 1.0 M solution of catecholborane in THF (7.62 mL, 7.62 mmol), via syringe. After stirring for 3 hours at 0°, the solution is quenched with methanol (15 mL), followed by addition of a solution 30% hydrogen peroxide (1.94 mL) in 3 M NaOH (18 mL). The solution is then warmed to room temperature over 3 hours. The solution is concentrated to 25 mL in vacuo, and the residue is taken up in H2O (100 ML) and extracted with ether (3×50 mL). The combined organic phase is washed with water (1×50 mL) and brine (1×50 mL), dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 4:1 EtOAc/hexane) yields N,N-diethyl (E)-3-[3-(3-hydroxypropyl)4-(1-phenylethoxy)-phenyl]-but-2-enamide.

Workup

  1. customthe solution is quenched with methanol (15 mL)
  2. additionfollowed by addition of a solution 30% hydrogen peroxide (1.94 mL) in 3 M NaOH (18 mL)
  3. concentrationThe solution is concentrated to 25 mL in vacuo
  4. extractionextracted with ether (3×50 mL)
  5. washThe combined organic phase is washed with water (1×50 mL) and brine (1×50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccc426789cbf4f6bb82c8b3f77d6942c
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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