HCID 67315923, compound → Ethyl β-methyl-2-naphthalenepropanoate

HRID 1014766Notes

Reaction equation

HRID 1014766 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH3:18])=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>[Ir].C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 67315923HCID 67315923, compound

Product 1

HCID 57055028Ethyl β-methyl-2-naphthalenepropanoateYield 99%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of ethyl 3-(naphthalen-2-yl)-but-2-enoate) (70 mg, 0.29 mmol) and iridium catalyst (S)-32 (9.2 mg, 0.0058 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 38 (70 mg, 99%) as a colorless oil. [α]20D −25.9 (c 1.02, CHCl3); CSP HPLC analysis (Chiralcel OD-H; eluent: 99.5:0.5 hexanes/i-PrOH, 1.0 ml/min) determined a 89.5:10.5 er (79% ee) [tR(minor) 12.34 min, tR(major) 14.19 min]; 1H NMR (300 MHz, CDCl3) 7.82 (d, 3H, J=8.4 Hz), 7.69 (s, 1H), 7.51-7.39 (m, 3H), 4.11 (q, 2H, J=7.2 Hz), 3.50 (sextet, 1H, J=7.5 Hz), 2.81-2.62 (m, 2H), 1.42 (d, 3H, J=6.9 Hz), 1.19 (t, 3H, J=7.2 Hz) ppm; 13C NMR (75 MHz, CDCl3) 172.3, 143.1, 135.5, 132.3, 128.1, 127.6, 127.5, 125.9, 125.4, 125.3, 124.9, 60.2, 42.8, 42.6, 36.6, 21.7, 14.1 ppm.

Workup

  1. customRemoval of the solvent
  2. customin vacuo and standard purification

Sources & evidence

ORD record
ord-534bff48ce4742908e4a2ad9a75fa60d
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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