trans-Stilbene → Dibenzyl

HRID 1014767Notes

Reaction equation

HRID 1014767 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 638088trans-Stilbene

Product 1

HCID 7647DibenzylYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of trans-stilbene (50 mg, 0.28 mmol) and rac-32 (8.8 mg, 0.0056 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 48 h. Filtration of the reaction mixture and evaporation of the solvent gave 39 (50 mg, 97%). mp 48-50° C. (lit.1 47-49° C.) 1H NMR (300 MHz, CDCl3): δ 7.39-7.25 (m, 10H), 3.01 (s, 4H); 13C NMR (75.5 MHz, CDCl3): δ 141.9, 128.6, 128.5, 126.0, 38.1.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent

Sources & evidence

ORD record
ord-e5d95157b47f48509c90ea6c4825a758
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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