Trimethylsilyldiazomethane → Methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate

HRID 22829Notes

Reaction equation

HRID 22829 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH2:8]([C:13]12[CH2:20][CH2:19][C:16]([C:21]([OH:23])=[O:22])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2)[CH2:9][CH2:10][CH2:11][CH3:12]>C(Cl)Cl.CO>[CH2:8]([C:13]12[CH2:18][CH2:17][C:16]([C:21]([O:23][CH3:1])=[O:22])([CH2:15][CH2:14]1)[CH2:19][CH2:20]2)[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 42414664-Pentylbicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 22591715Methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(Trimethylsilyl)diazomethane (2M/hexane, 53 mL, 106 mmol) was added slowly to a solution of 4-pentylbicyclo[2.2.2]octane-1-carboxylic acid (2-A) (20.3 g, 90.6 mmol) in methylene chloride (100 mL) and methanol (40 mL) until the yellow color persisted. After stirring for 10 min at room temperature, the solution was concentrated in vacuo to give methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate (2-B). 1H NMR (500 MHz, CDCl3): δ 0.89 (t, 3H); 1.20 (m, 8H); 1.39 (m, 6H); 1.77 (m, 6H); 3.65 (s, 3H) ppm.

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-75301ea7f92e43b1b3711118cb633278
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

Loading…