Tributylstannane → 2-Propenoic acid, 2-(tributylstannyl)-, methyl ester

HRID 970331Notes

Reaction equation

HRID 970331 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9].[C:14]([O:18][CH3:19])(=[O:17])[C:15]#[CH:16]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:6]([Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:10][CH2:11][CH2:12][CH3:13])[C:15](=[CH2:16])[C:14]([O:18][CH3:19])=[O:17])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 13536Methyl propiolate

Product 1

HCID 109597232-Propenoic acid, 2-(tributylstannyl)-, methyl esterYield 41.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A degassed solution of Bu3SnH (8.73 g, 30 mmol) in dry THF (40 ml) was added during 40 min to a degassed solution of methyl propynoate (2.52 g, 30 mmol) and Pd(PPh3)4 (0.693 g, 0.6 mmol) in THF (40 ml). The resulting mixture was stirred for 3.5 h at room temperature under nitrogen. THF was then removed under reduced pressure and the residue was diluted with hexane (200 ml). After 12 h, the mixture was filtered on celite and the filtrate was concentrated under reduced pressure. The residue was diluted with hexane (200 ml), filtered on celite and concentrated. The residue was purified by silica gel column using hexane/EtOAc (98/2) as eluant to give 4.7 g of 337B as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ 6.89 (d, J=2.64 Hz, 1H), 5.92 (d, J=2.64 Hz, 1H), 3.74 (s, 3H), 1.60-1.20 (m, 12H), 0.97 (t, J=8.34 Hz, 6H), 0.89 (t, J=7.03 Hz, 9H)

Workup

  1. customTHF was then removed under reduced pressure
  2. additionthe residue was diluted with hexane (200 ml)
  3. waitAfter 12 h
  4. filtrationthe mixture was filtered on celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionThe residue was diluted with hexane (200 ml)
  7. filtrationfiltered on celite
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-64b248f777d1487bb35843c5aec508c2
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

Loading…