1,4-Naphthoquinone → 2,3-Dihydro-1,4-naphthoquinone

HRID 1014773Notes

Reaction equation

HRID 1014773 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[CH:10]=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1>C(Cl)Cl>[C:7]1(=[O:8])[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:11](=[O:12])[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 85301,4-Naphthoquinone

Product 1

HCID 114805992,3-Dihydro-1,4-naphthoquinoneYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of naphthoquinone (50 mg, 0.31 mmol) and rac-32 (10.0 mg, 0.0063 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 72 h. Filtration of the reaction mixture and evaporation of the solvent gave the crude product, which was purified by column chromatography (30% EtOAc in hexane, silica gel) to give 47 (45 mg, 89%) as a 2:1 mixture of 2,3-dihydronaphthalene-1,4-dione and 1,4-dihydronaphthalene-1,4-diol. 1H NMR (300 MHz, acetone-d6, 2,3-dihydronaphthalene-1,4-dione33): δ 8.00-7.97 (m, 2H), 7.83-7.81 (m, 2H), 3.11 (s, 4H); 1,4-(dihydronaphthalene-1,4-diol34): δ 8.32 (bs, 2H), 8.18-8.15 (m, 2H), 7.47-7.43 (m, 2H), 6.73 (s, 2H).

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent
  2. customgave the crude product, which
  3. customwas purified by column chromatography (30% EtOAc in hexane, silica gel)

Sources & evidence

ORD record
ord-a477100c4c8047efbffcd26c029a6833
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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