Triethylamine → 1-Indanone

HRID 1504936Notes

Reaction equation

HRID 1504936 reaction equation
[2H]C1C([2H])=C([2H])C(B(O)O)=C([2H])C=1[2H].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C.[C:68]1(=[O:77])[C:76]2[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=2)[CH:70]=[CH:69]1>O1CCOCC1.O.[B-](F)(F)(F)F.C1C2C=CC1C=C2.C1C2C=CC1C=C2.[Rh]>[C:68]1(=[O:77])[C:76]2[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=2)[CH2:70][CH2:69]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 634876Binap, (A+-)-HCID 118153841H-inden-1-oneHCID 16213772Phenyl-d5-boronic acid

Product 1

HCID 67351-Indanone

Reagents, catalysts & solvents 2

HCID 10915722Bis(norbornadiene)rhodium(I) tetrafluoroborateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of compound A (57 g) in tetrahydrofuran (600 mL) was added triethylamine (30 mL) dropwise over 30 min. The reaction mixture was kept at room temperature for 3 hours. The precipitated solid was filtered and the filtrate was concentrated in vacuo. The residue was reprecipitated from diethyl ether to afford compound B (31 g) as a yellow solid. To a solution of compound phenyl-d5-boronic acid (25 g) in 1,4-dioxane/water (900 mL/90 mL) was added [Rh(ndb)2]BF4 (1.3 g), racemic BINAP (2.1 g) and triethylamine (14 mL), then the reaction mixture was kept at room temperature for 2 hours under N2. Then compound indenone (19 g) was added, and the resulting mixture was heated to 100° C. for 3 hours. The precipitated solid was filtered off. The filtrate was concentrated in vacuo. The residue was purified by chromatography to afford indanone C (10 g).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-0b1acbdd4a3048dd98572645e4f40659
Source dataset
uspto-grants-2015_12
Patent number
US09216961B2

Reaction notes

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