HCID 86690122, compound → HCID 86690124, compound

HRID 520418Notes

Reaction equation

HRID 520418 reaction equation
[CH2:1]([O:4][C:5]([CH3:16])([C:11]([F:15])([F:14])[CH:12]=[CH2:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C=C>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[F:15][C:11]1([F:14])[CH:12]=[CH:13][CH2:1][O:4][C:5]1([CH3:16])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 86690122HCID 86690122, compound

Product 1

HCID 86690124HCID 86690124, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred de-gas solution of ethyl 2-(allyloxy)-3,3-difluoro-2-methylpent-4-enoate (165 mg, 0.704 mmol) and Grubbs II (29.9 mg, 0.035 mmol) in DCM (20 mL) was stirred at rt overnight. The reaction mixture was evaporated to dryness and purified by silica gel FCC (2% EtOAc in hexanes) to afford ethyl 3,3-difluoro-2-methyl-3,6-dihydro-2H-pyran-2-carboxylate as a clear oil (˜138 mg, 95%). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 6.26-6.20 (m, J=10.5, 2.4, 2.4 Hz, 1H), 5.96-5.87 (m, 1H), 4.57-4.48 (m, 1H), 4.36-4.26 (m, 3H), 1.60 (s, 3H), 1.33 (t, J=7.2 Hz, 3H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by silica gel FCC (2% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3ca778308af94350b45763baf84f4c04
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

Loading…